Mai Allen says “I just love this house because it is so beautiful, but it was not my choice to move out here.”

When my husband and I first moved to San Diego two decades ago, we were full of midwestern optimism — I refuse to call it naivete. Aaron had secured his first job out of college, working as an engineer in Point Loma. I pictured us settling down in a quaint beach bungalow, watching the sun set over the Pacific while sitting in oversized wicker chairs on our back patio. Our kids would be perpetually sun-kissed. Birds of Paradise would line our white picket fence. Our tub would be forever ringed with a thin line of sand.

Madigan Brigg’s Spanish-style Kensington rental home is adorable. It has curb appeal. But it’s not exactly the type of home you would imagine three twenty-something guys and a 25-year-old girl living in.

That’s not exactly how things played out. After arriving in San Diego, we lived at the Motel 6. My husband’s new company footed the bill while we attempted to find the perfect rental. We had done little research prior to moving — optimism! We simply packed up our station wagon, carving out just enough room in back for our four-month-old son and our overzealous Labrador Retriever puppy, and set off cross-country. We knew nothing about San Diego’s different neighborhoods, other than what my husband’s college roommate had told us. David, a trust fund kid, had spent one year living in the dorms at USD before transferring to Kansas University for his sophomore year. Here’s what he told us: “Everywhere in San Diego is nice, just not El Cajon. Rent a little place in Ocean Beach; you’ll love it.” If memory serves, this advice was given in between bong hits. Armed with this knowledge — and the aforementioned optimism — we headed west.

So: Ocean Beach. Shortly after our arrival in San Diego, Aaron steered our station wagon down Newport Avenue. I watched out the window as the antique stores and bars slid past. There were buskers and leathery folks in tie-dyed clothing hanging out on the sea wall. There was a drum circle on the grass. A toddler chased bubbles before collapsing into a fit of giggles. This is it, I thought. This is where we will end up. I was wrong. The beach rentals we found were absurdly expensive — and remember, this was 20 years ago. We couldn’t afford a two-bedroom in OB — or anywhere coastal, for that matter. We began searching further east, stopping just shy of David’s dreaded El Cajon. We settled in Spring Valley, at the base of Mount Helix.

In those early days, we spent hours driving around San Diego, exploring enclaves, dreaming about our future, wondering where we would land. Aaron hoped to end up in Point Loma, close to his work and the water. I still dreamed of Ocean Beach, though I was also charmed by the Craftsman houses of Mission Hills and South Park, the mellow coastal towns in North County, and the sleepy little village section of La Mesa.

About a decade of renting later — in Spring Valley, then El Cajon, and then Tierrasanta — we had managed to save enough for a down payment on a home. We started our search in Point Loma and Ocean Beach — some dreams die hard when you’re an optimist. Again and again, we were outbid. We broadened our search. Scrolling through real estate online late one night in 2011, I found our house. Walking distance to downtown La Mesa — I knew the neighborhood well from those early drives. As soon as we set foot inside, it felt like home. We offered above asking price and bought the place for $360,000. (The previous owners had purchased it in 2004 for $465,000.) Four beds, three baths, just over 1600 square feet, with a sizeable yard, a big climbing tree out back, and an oversized window in the living room with a gorgeous view. The kitchen and bathrooms were ‘70s flashbacks, the exterior was painted bright pink, and I didn’t care. It reminded me of the my small hometown outside of Chicago. It smelled like freshly cut grass. The day we toured, I heard the sound of children playing in a nearby backyard. It was perfectly us.

A decade later, I still love our house. Currently, Zillow has our home’s worth estimated at $930,000. While I am impressed by the rise in value, the steep increase makes me melancholy. We could never afford it now. My heart breaks for those wide-eyed Midwesterners who might stumble out here the way Aaron and I did, full of optimism and dreaming of home ownership. Many of them will be priced out of San Diego’s housing market entirely. Out of curiosity, nostalgia, and the fear that my own children will never be able to afford to buy a home in their own city, I took to the streets to ask locals about their housing situations.

Mai Allen

Age: 46

Occupation: Sr. Project Manager & Vice President at MUFG Union Bank

Location: Valley Center

Mai is what not who comes to mind when I think of Valley Center. Her nails are manicured, her makeup is immaculate, her long, nearly waist-length brown hair is perfectly curled, and she drives some sort of luxury car that appears to have been freshly waxed. Her friends and family refer to her home’s location as “the boonies.” But it should be noted that, in true Mai fashion, her home sits on five acres, is a whooping 3500 square feet, is outfitted with a pool and a hot tub, and is located inside a gated community. “If it had been up to me, Dan and I would have bought a bigger house in Rancho Bernardo, not moved here,” Mai says as she gives me a tour of her ranch-style home. She reiterates: “I just love this house because it is so beautiful, but it was not my choice to move out here.”

When I arrived here, I was buzzed through her community’s front gate. I drove up a winding road and admired the stunning mountain views. Near the top, right before I turned into her driveway, I stopped for a wayward road runner leisurely crossing the street. I turned left and passed through Mai’s iron security gate before parking my car behind her 23-year-old’s Tesla. I then found I was too scared to get out of my owncar, because two humongous Italian Mastiffs were circling it. “They just look scary; they are harmless,” Mai shouted from the doorway, her voice bubbling with laughter. When I hesitated despite her reassurance, she laughed harder and walked toward the car. She was wearing platform sandals, so she should have looked taller, but in comparison to her dogs... We slipped into her home. “You are not coming inside,” she shouted, waving a finger at the Mastiffs before shutting the door behind us.

Now, I’m following Mai down a tiled hallway and into a window-strewn kitchen that looks out at a pool and acreage beyond. Mai tells me that this is the third home she has owned in San Diego. She bought her first with her then-husband in the early 2000s, when she was just 23 years old: a two-story, two-car garage, El Cajon house in Granite Hills. After divorcing, she and her ex-husband sold it in 2008 — at the bottom of the market. “We didn’t really make anything off the sale because it was during the housing crash,” she recalls. “I didn’t really care. I just wanted to get out of there because of the divorce.”

In May of 2008, Mai and her boyfriend Daniel Allen, who would later become her new husband, decided to buy a place together. “Dan and I both wanted our kids to attend good schools. I wanted them in the Poway school district. So we bought a house in Rancho Bernardo for $456,000. At the time, that seemed like a lot of money to me. We ended up selling it in 2019 for about $700,000 — to a cash buyer.” Rancho Bernardo had been a drastic change from El Cajon. “It took me awhile to get used to it, but after a while, I really, really, liked it. The kids are a little bit snottier. Racially, it is really a lot of white people, and Asians, and some Indians. You don’t see a lot of [diversity]. But they have nicer schools.”

When her son graduated from high school and Dan’s teen daughter moved in full-time with her mother, the Allens decided to look for a new house. “My husband did not really like neighbors,” Mai says, tilting her head back and letting out a sprinkle of laughter over the memory. “He liked privacy. That was just his way. He didn’t want to have to deal with people. Living in Rancho Bernardo was so convenient, but our neighbors were literally [on top of us].” If it had been up to Dan, the two of them would’ve headed out of state; he wanted to live in Texas or Arizona. He wanted his own slice of land. Mai was indifferent about the land, but not the location. “I said, ‘I am absolutely not leaving San Diego! You can leave if you want! I am staying here! My family is here, my friends, my career, everything is here.’ Luckily, he decided not to leave me!” Mai says, laughing again before continuing, “We compromised.”

They began their search in Ramona, Bonsall and Valley Center. “I ruled out Ramona because of the frickin’ weird ass people there. Not that I am totally normal, but I am not that weird. I ruled out Bonsall too, because once again, weird people, and it’s way too far. We looked at a few homes in Valley Center. Most of them were deeper in Valley Center. I told Dan, ‘I am not moving anywhere that is that far away!’” Eventually the pair found their current house — in the boonies, but not so far out in the boonies that it is wildly inconvenient. It still feels connected to civilization. When Dan and Mai attended the open house, there were features about the home they both loved. Mai liked that it was in a gated community. Dan liked the fact that it was on five acres. They both liked the pool. “After the open house, I told Dan, ‘Here are your choices: we move into this house, or we don’t move!’” Smile lines form around Mai’s eyes.

The Allens put in an offer of $899,000. It was accepted, and they moved in April 2019. The home is currently valued at $1.3 million. “We bought this house because Dan had no other choice,” she says with a chuckle while ushering me through a sliding glass door to the backyard. “Down there we have avocado trees,” she says, pointing past her pool and into a sloping valley below. “I said to Dan, ‘If we are going to move to Valley Center, this is the house.’ I fell in love with it when I saw it. The only thing I did not like was that it was owned by a couple in their late seventies. The appliances were old. The refrigerator was rusty. I was like, ‘We are not putting food in that!’ We bought all new appliances. We spent a lot of money upgrading the house. They had tan carpeting that they let their Jack Russell pee all over. We redid the floors. It’s getting there, but I have more to do. We signed a contract for a full remodel a few days before Dan died. So, I put that on hold…. for now,” Mai says her voice trailing off. Tragically, Dan passed away in September 2022. He was 41 years old. He was driving his motorcycle home from work when he was struck by a car, and died at the hospital a few hours later.

Standing in her yard, listening to the birds’ chirp, Mai tells me that she cannot imagine moving — ever. “I really love it here. I love the big windows and all the light that filters in. My master bedroom is an oasis. I can close the door and be in there all day. I love being able to walk out in my backyard naked if I want — because who is going to see me?”

Jon Losee

Age: 83

Occupation: Retired, former physicist

Location: Point Loma

Jon Losee still skis in Tahoe every winter. He is old enough that he doesn’t have to pay for a season pass; they just give him one. And in the summer months, Jon and his wife Debbie scuba dive in fun locales like Cozumel and Tahiti. So when Jon explains that he built his own house in Tahoe when he was just 19 years old, I am not surprised. Nor am I surprised to learn that he also built the two-story Point Loma home he has lived in since the 1970s. When he details the adventures had while building his homes, Jon’s eyes twinkle and he seems like a much younger man.

“You are not coming inside,” Mai shouted, waving a finger at the Mastiffs before shutting the door behind us.

In 1972, one year out of grad school, Jon Losee was offered a job at the Navy Lab in Point Loma. “When we first moved out here” — with his first wife and their children — “we rented an apartment off Balboa Avenue in Clairemont. Prior to that, I was renting a big two-story house in Nebraska for $105 a month. I don’t remember how much we rented the [Clairemont] apartment for, but it was more than that. Very shortly after that, I was sent to Hawaii for three and a half months to work at the lab there.”

While in Hawaii, Jon’s rent was covered by work, and he sublet his San Diego apartment. “When I got back from Hawaii, [work] decided to pay me full per diem, seven days a week, the whole time I had been Hawaii! I got a big check from the government. That is how I was able to buy this house.” Jon explains while we sit at the kitchen table in his Point Loma home. He takes a glass out of one of the pine cabinets he constructed himself as a young man and pours me a glass of water.

In 1973, the San Diego housing market was hot. People were buying up properties sight unseen. “We paid $33,005 for our house. That was a lot for the time. It was a two-bedroom, one bath, and about 800 square feet. I could’ve bought a 1500-square-foot brand new house in Scripps Ranch for that price. But I bought in Point Loma because it was by my work. I don’t have the personality to commute that far every day. They were asking $25,000 for the place, but in those days, you had to up the asking price.”

Jon had big plans for his little house: he added a second story and turned it into a four-bedroom, 2300-square-foot home. In total, the renovation cost him around $20,000. “We did not have the money to hire help. I tore the roof off the house and threw it in the backyard. People thought I was nuts. It was off for like three or four months.” But Jon knew what he was doing. He had gone through the process of building a home when he was a teenager. Adds Debbie, “Jon built his place up in Tahoe before this. But the Point Loma house was a much more ambitious project.”

Jon nods his head, smiling at the mention of the cabin, which now serves as his daughter’s family home. “I purchased that land in Tahoe for $1750 in 1960. I was too young to buy a lot, so I had to put it in my dad’s name. I was working a union job at a grocery warehouse so I thought, ‘Okay, I can pay this off in a few months.’ It was paid off in 6-8 months. I was attending Sacramento State, so I used my summers off to build. In the fall of 1960 we put in the foundation, and the summer of ‘61 and ‘62 we basically finished it.”

When Jon says “we,” he is talking about his dad and his dad’s buddies, who would sometimes drive out to offer a hand. Jon also had an assistant, a man recruited from the Labor Hall in Sacramento. “I didn’t pay him. All I could offer was room and board,” Jon laughs, noting that “room” consisted of a tent, a table, and a makeshift latrine sectioned off by two tarps hung on trees. “He was an old Norwegian guy, an odd character. He didn’t drink at all for maybe six weeks or so, and then he would go on a bender. That was the type of alcoholic he was. In a way, it worked out, because when he was dry, we could get things done.”

Since Jon was so young, people were eager to help and teach him. “The building department was a couple of miles away. Inspectors started dropping by my place while they did their rounds. They were really very helpful. I would ask them questions. I would say, ‘I am curious how would you do this?’ They loved it. They would come in and get right down to the dirt with me and [teach] me all these things. They would stop by almost every day. I learned a lot.”

Back in San Diego, during Jon’s Point Loma build, the building inspectors were not quite as helpful. After he secured his building permit, city inspectors started stopping by. “The inspectors were typically ex-contractors. They didn’t like amateurs. An inspector came over one day, all grumpy, and started looking around. I had built this beam,” Jon says, pointing to a beam near the stairway in his home. “I had somehow cut the beam into another one, no screws. It’s notched. I can’t even remember how I did it. The inspector looked at it and said, ‘That is the most beautiful thing I have seen in years.’ After that, they just signed off on it. They didn’t bother me again. I built it primarily by myself, but friends and family helped.” In total, the Point Loma house took Jon four years to compete — he had a full-time job and no longer had entire summers off.

“Finishing this house was very empowering.” he says. More than 50 years later Zillow values it at $1.7 million.

Max Powers

Age: 38

Occupation: Sales

“My parents bought me my first house when I was 22 years old.” Max explains while sitting on his girlfriend’s sofa. He recently moved in while his condo — an 800-square-foot one bedroom — is being renovated. “The house was in Serra Mesa. My parents bought it there because that is where they grew up and it’s conveniently located. To be perfectly honest, they bought it thinking I would have a family by now. They bought me a family starter home and I never got a family,” He shrugs and lets out a laugh at the absurdity.

Living in Serra Mesa was not ideal for a young man. It wasn’t hip. There weren’t many bars or restaurants. Max saw the three-bedroom home as too much house. “I needed a change, so I sold it in 2018. Three years prior to me selling my house, [our parents] bought my brother a place up the hill in Serra Mesa. He made $250,000 selling his house and it was just two miles away from mine. But my side of Serra Mesa, maybe because it was closer to the freeway, or it was near a power substation, didn’t increase much in value. I sold it for $675,000. [My parents] bought it for $580,000 in 2005. Considering the upkeep on that house, I basically maybe made $30,000 on it. I never had to pay a mortgage because my parents paid it right off. I just had property taxes and maintenance, but that shit adds up!”

Max laughs to lighten the mood, but it is evident that the condo is a very sore subject. “Tacking on permits, appliances, hardware, lights, floors, furniture — I would estimate the whole thing is costing me $130,000.”

After the sale, Max set his sights on Crown Point. He liked that it was near the water but not near all the bars and parties in PB. It was quiet but not boring. He found a small condo there listed for $550,000, put an offer in, but didn’t get it. He told his realtor to keep an eye out if another condo in that complex went up for sale. “Eventually, another condo in that complex came on the market. It was cheaper, listed at $520,000. I put in an offer of $480,000 and got it.” It’s hard to tell by his demeanor if he is happy about the purchase.

“It was a great deal, but it has never been upgraded,” he notes. “It’s run down — terrible carpeting, half the lights don’t work, the outlets don’t work, the oven sucks, the fridge didn’t even have a handle. It was fucking shit! It’s like one of those places where you buy it, put 20 grand in, and it’s now worth $100,000 more. I got it at the right time. In my unit, you can see the SeaWorld fireworks from my couch. The other one I was looking at was one floor up on the other side of the building. I would not have been able to see the fireworks from my living room. So, whatever, I got lucky.” He shrugs.

In July 2020, one week after his move in, Max attempted to begin the renovation process on his outdated condo. “Demolition [on my condo] started today. TODAY! July fucking 14th, 2020 was when I started this renovation process, and it’s May 10th, 2023!!” He goes on, softening his voice but clearly still irritated, “I am hearing conflicting reports on why it has taken this long. Basically, it’s a zoning thing. Trying to start [renovations] during covid delayed things. I have a very pessimistic attitude about all of this. It’s hard to be optimistic about any of what I have been going through.”

Through clenched teeth, Max adds that his contractor has already called him to report a problem, “One of the walls I was going to tear down is load bearing. My price point just jumped about $8000!!”

“Can’t you just keep the wall?” I ask.

Max grimaces, “IN MY PLANS, THE WALL IS GONE!!” He takes a deep breath and settles down a little before continuing. “If the wall is there when an inspector comes, I am fucked! FUCKED! I’ll have to change permits! You can’t just change permits! This has been the fucking delay! The permits! Don’t get me started on this shit!” Max laughs to lighten the mood, but it is evident that the condo is a very sore subject. “Tacking on permits, appliances, hardware, lights, floors, furniture — I would estimate the whole thing is costing me $130,000.”

“That is a lot,” I say, more to myself than to Max, and he nods.

“I am thinking about selling it eventually. I would like to get a yard for my two dogs. It would make my life easier. I see myself living [in the condo] for three years at least. I think a one-bedroom in this place goes for $650,000 now. Renovated, I could sell it for $700,000. I’ll probably hold on to it, maybe buy something else and rent it out.” By this point, he has chilled out about the permits. He is reclined on the couch with one of his dogs cuddled up next to him, his eyes on a baseball game on the TV.

Madigan Briggs

Age: 25

Occupation: Marketing and sales

Location: Kensington

Madigan Brigg’s Spanish-style Kensington rental home is adorable. It has curb appeal. But it’s not exactly the type of home you would imagine three twenty-something guys and a 25-year-old girl living in; it looks more like the type of house where you’d find a pair of young professionals just starting out in the world

The Kensington house is Madigan’s third San Diego rental. After graduating from UCSB in 2020, she moved in with her parents during the pandemic. In April 2021, she moved into a two-bedroom La Mesa apartment with her old college roommate for one year. “I paid $890 a month. We split the gas and electric and Wi-Fi, averaging around $60 a month each. I was finding it hard to get by. I was teaching preschool and not making a lot. When I started working at my current job, it got a little better, but not much — just better to the point where I wasn’t stressed out at the end of each month anymore.”

Madigan cut costs by cutting back on going out and buying cheap food. “I ate a lot of pasta. I figured out a pasta-vegetable meal that was kind of healthy. I could make it last for days. I would eat that and yogurt for like four days straight. I added whatever vegetable was in season, because that would be the cheapest. I bought random store brand pasta —the ones that are like 99 cents.” She chuckles at the memory.

In June of 2022, her roommate decided to move back to Fresno. “A friend of mine was moving into a house in City Heights. One of his roommates was leaving and looking to sublet his room. The rent was going to be $80 cheaper than what I was paying in La Mesa, so I sublet his spot.” But she and her roommates lasted only four months in City Heights, due to a cockroach infestation. “It was so gross. There were cockroaches literally everywhere. The kitchen had them, the living room, the bathroom. They were coming up from all over the place. It was disgusting. Our landlord was not really fixing the problem at all. She would put cockroach traps down, but there were tons of them. One cockroach trap was not going to do anything. So yeah, we decided to look for somewhere else to live.”

Finding a four-bedroom house to rent in San Diego was hard to do — especially one within their price range. Madigan says they started wondering if they would have to stay in the cockroach house. The place the roommates eventually found was initially listed at $6100 a month. “It was out of our price range, so we didn’t even look at it. But then they bumped it down to $4595 a month. We immediately went to look at it. We told the landlord we wanted to move in. He sent the contract over that Friday. We signed on Saturday. We moved in four days later. It was a ridiculous turnaround time.”

While Madigan loves the house, the rent was a big increase. Her monthly rent is $1200, and utilities are around $100. “Living at the old house in City Heights was the best I felt financially. I was able to save money. It was $400 cheaper, and our utilities were lower. Moving here has been a huge bump in my monthly expenses. I was not entirely ready for that. It was a little bit of a shock to my monthly allotment of money. But now, six months after moving in, I feel like I have more of a handle on it.” She loves that there is a coffee shop nearby, plus fun restaurants and bars. More importantly: no cockroaches.

When I ask Madigan about her future in San Diego, she is not an optimist. “Being able to buy a home here [in San Diego] is not something I ever truly believed I would be able to do. Growing up here, I have seen how expensive housing is. I don’t see a feasible way to buy a house unless I move to, like, Montana,” She and her boyfriend plan on moving in together in the fall; these days, they are casually looking at rentals. “I think we are more or less okay with living almost anymore. There is nowhere that I would never live. But I would like somewhere walkable, somewhere like Kensington, where I can walk to a little bar or coffee house. Originally, when we first started looking, I wanted to live in South Park. That is where I eventually want to buy a house. But it is so expensive! We have looked at some properties there. We took our Zillow filters off just to see what’s there. In South Park, a 450 square foot studio is going for like $3300 a month. It is truly ridiculous.”

Despite the expense, she and her boyfriend still discuss the possibility of someday buying something together. “We have talked about it, but not anytime soon. In a few years from now, maybe we could buy a two-plex, fix one part, rent it, and live in the other part. We could eventually sell that and then maybe we will have money to put a down payment on a home in San Diego. Our families live here. We are too spoiled growing up in San Diego to not stay here forever.”