The only halfway decent landlords I have ever had were boomers. (Although admittedly Joe O'Donoghue in SF was once my landlord and not a good one.)

Some of the worst?
The children of those boomers. Inherited the property. Immediately jack up rent and do less maintenance.
People love to knock Boomers, and their parents. But many of them have a much longer and less extractive and more humane view about business even when they are in an exploitive relationship because of the times they lived in.
Granted, the Boomers parents were more humane if they lived through the depression and had personal hardship then. Half my family from then were Socialists who got black balled for it. The other were - well - republicans, sadly.
But both sides of my family's elder generation became skeptical of the heavy corporatization and greed that occurred in the 80's and 90's.

The conservatives in the younger generations went further rightward.
Anyway, just thinking about generational politics in the bay area, small time landlords, and their children and the very different attitudes people have over the past 20 years here, a period with hellacious gentrification, and loss of a once much richer culture and way of life.
I think the single greatest contributor to undermining Bay Area's once vibrant culture (and once far far more diverse) has been the increase of rents and aggressive development to capitalize on it. The two have always gone together. Rather than reverse as YIMBY's claim.
Parties in my house growing up were neighborhood affairs which had people from totally different backgrounds. Our mailman - a reticent older dude named Bob - drank at the local bar where my dad would go with friends sometimes. And they hung out. This is Oakland.
When I was married I socialized like a gentrifier - with a very narrow band of people. People with advanced degrees and high paying jobs for the most part. And not from here. I was the local, and usually the only locals we socialized with were my friends - not randoms.
Thats a fucking sea change just because the rents are so fucking high that the requirements of living here push you into specialized work and narrower social circles, and a narrower way of looking at the world.

Think again about those younger landlords.
Now that I am not married, my social life drifted back towards real people and away from gentrifiers, but I am now locked into (due to child support payments and my disdain for designing gardens for rich people) a higher income profession: tech, which restricts my connections.
Anyway, professional class attitudes about the economy and what you deserve from it are very very different than people who clean your homes, tend your gardens, change your IV, and check you out at the grocery store.

Gen X landlords adopt those attitudes and expectations.
Gen X landlords look at the property as income, and tenants as a hassle. Because you can sell the fucking thing for a shitload. You can in some neighborhoods go the AIRBNB route with a much higher rate. Or do both. AIRBNB shack in the yard, and maximized rent on the rest.
These Gen X landlords are not people who are thinking about just having a stable investment for 40 years. They are wondering if the world will be here in 40 years, and much much more cynical. How can they get their shit out now, and enjoy what they have now?
Gen X landlords are not thinking about being part of a rich Oakland neighborhood. There has been so much development going on that Oakland is not the Oakland they grew up with. And their people are not here any more. They are thinking about themselves and other places.
After 2000 in Oakland I was amazed at how many old Black families who owned property sold their property or otherwise used it to finance moving out of the city.

When I grew up I was usually the minority (racially) at a party. And schools were far more equally mixed.

Not so now.
Anyway, rapacious gentrification isn't just huge corporations bulldozing your city and tech bro libertarian racists moving in. Thats definitely a part of the scene (especially SF's) but its also just people becoming more cynical and short-sighted due to the times we live in.
The 40's through the 60's were a time of much more prosperity. And if you weren't the subject of the few developments which tore up African American commercial districts, they were stable times allowing a longer term view. Investment in your community.
But anyone born in the 70's or later has not had this. Prop 13 gutted our education opportunities. Corporate jobs enabled lots of people to move away so the 80's saw lots of "white flight" and disinvestment. And this was coupled with a a rapid dwindling in manufacturing jobs.
My babysitters and elder neighborhood kids for example had a totally different experience at Oakland and Skyline High Schools.

They had robust sports programs. Auto-shop. Home econ classes. Tons of local awards, sponsorships, internship opportunities etc...
When I was in elementary school. The roof of my classroom fell in from rain one year. And on three other years our teachers were out on strike for much of it because the district refused to give them agreed upon raises. Austerity hit hard.
The mothers at my somewhat affluent Elementary School (Glenview) had to go and get some of the text books that were unwrappd in storage because there weren't people around who even knew what was there, and the people in charge (corrupt at the time) didn't care.
We only had art classes because my mom taught art for free and ran a school wide art "show" called Spring to Me which replicated throughout some of the district, and brought in loal news affiliates to get it on the news for us. We got our art on the local station.
My mom could only teach art for free because we were fortunate enough to have really cheap rent which we were lucky to turn into a mortgage. The house cost only $25,000. Which my dad who was a professional musician when I was born was able to just barely afford.
No, my dad made almost nothing as a musician. We lived hand to mouth until he learned to hustle like the yuppies and eventually become one in the 80's.
I don't know anyone who lives here now - certainly not in the neighborhood around Glenview - who has a father who didn't graduate from college and tried to make it as a local musician playing in bars - and mother who made a living as an artist and art teacher. Total bohemian life
And we had a place to live. Did not rely on other income from the broader family. And two kids. In fucking Glenview.

The house only cost $25,000.
Compare that to the people living here. Every new person is a double income professional family with at least one but usually two advanced degrees. And $250k a year jobs. Homes cost from $700k to over a million.

Little fucking bungalows on .10 acre.
What happened? In many cases, those people who moved away working jobs at multinational or national corporations in the 80's? A lot of them came back.

I rent a place not far from the Lutheran Church in Glenview. When I was a kid this was the conservative's church.
People drive in to go to that Lutheran Church, and tell me how they went to that church as kids. People that haven't had a significant connection to the neighborhood for decades.
These aren't people who ride bicycles or the bus.

On the same street the old folks home has a special German Daycare program thing.

Same economic class. But not locals go there. BMWs. Mercedes. Germans nationals working in the Bay Area along with white yuppies.
All of the people I grew up with who still live here:

inherited the house and now live in it.

My great grandmother's best friend died a little after 2000. Her grandson - my first Dungeon Master at that very house - now lives there.
There was a house up the street with a roof that had literally caved in. I knew the owner. And was trying to get him to sell it to me for cheap since I could actually do the work myself to make it livable.

He sold it to a flipper instead.
I was about to start talking about the politics of these people and their general attitudes, but its too much personal info.

In general, to sum up, my experience is that the economy is too cut throat for most to consider community important.
The guy I was negotiating with really weighed selling the house to me. But he cut off communication because he also had siblings to consider and their desire for all that fat cash instead of selling to me as is for less than $200k.
The dude however thought about it, and then had to ghost me. Because he couldn't tell me that the money was more important to him than selling to a guy he knew, and visited with him once in that very house. He said that mattered to him a lot.
Another property in the neighborhood:

A cottage. One bedroom. A woman lived there until about 4 years ago. The mold got bad. Roof leaked. Not a major repair, and she was tolerant, but after absolutely nothing for a long time from landlord she got sick and had to move.
I wanted to move into that cottage. Look into fixing the problem. A cottage is easier to handle. And it had a great garden. Landlord refused to talk with me. Immediately put it on market for about $400k. I thought it would never sell.
The little cottage was bought, and rather than make use of it for such a high price (because it wasn't worth that). They managed to max out development on the lot into a two story structure by completely leveling the property out and selling for profit to some rich kids.
The prior tenant had a great garden there. Lemon tree. Chickens. Honey from bees. And tons of vegetables. And connected with the other people who do bee keeping in the area and so on.

That property now: almost no dirt.
When I moved back to Oakland back in 2004, I did landscape design and installation. And initially had enough free time to do volunteer restoration work and pro-bono design - even a monument installation in a local park for free.

But my income was only about $30k.
Just to survive, by 2005-2006 since I had no support and had to support someone who wasn't working, I gave up working for myself and probono stuff, and had to go work for a firm as a designer.

Income goes to $60k.
While making $60k as the sole income for a family of 4, I rented the cheapest place in Glenview with a leaking roof.

And I never was able to go to the dentist. Didn't eat 3 meals a day. And never went to a doctor. Did not own a car.
That marriage of course failed because I resisted selling out further. Resisted at my job working on market rate housing projects (I did public schools mostly), and wanted to get back to working for myself.

I never made median income for a family of 4.
So how did I try to save my marriage, I transitioned to tech.

That failed for reasons and changing careers is risky, but after 5 years I finally make enough money to rent a place without a leaking roof, and plumbing that is almost rusted all the way through.
hat I am saying is that in order to rent a nice apartment in the neighborhood I grew up in (where I grew up in a house with a full family and bohemian artist parents) I had to completely sell out and work as a software engineer.

Income is already more than I could have imagined.
But software engineer income by itself to buy a $1.3 million cottage?

not enough.

enough to rent an overpriced Glenview apartment. Enough.
I don't know how to impress upon anyone the amount of coersion that the Capitalist economy and gentrification puts upon people other than telling the above story. And I still am not sure I've made the point.

I'm a spoiled, white middle class kid of former hippies.
I started this rant about landlords who are the children of landlords because I think it also expresses the profound change in culture and attitudes which has happened here.

I sold my soul after decades of grudging resistance and sacrificed health and marriage, but that is rare.
My path is that of a loser. I walked a middle road where I could work a job that made just enough to survive and did marginal good, or at least little harm. And I failed because I couldn't hold my marriage together with that pressure.

No one I grew up with did the same.
Everyone I grew up with. Or went to college with. Considered my absolutely crazy. (I was the one everyone expected to make a million dollars because I was programming computers in the 80's for fun). Instead I ran the other way, but still had to earn a living.
Just to impress upon you how stubborn I am. I refused to let my parents pay for my college education because they gave me shit about how hard it was and tried to micromanage me.

I worked many jobs and took 8 years to get through.
And yes after multiple years doing things like working in Agriculture in the Central Valley on minimum wage, I finally wised up and learned web development to pay for it.

but anyway. I am stubborn as fuck. Like manual labor. And learning by working that way.
I know no one who has remotely gone the same path like me from a privileged background. And I fucking failed hard.

And then I eventually after decades and sudden health warnings gave in and learned the latest software bullshit and took 5 years to transition well into middle age.
So maybe I can buy health insurance now and deal with the absesses in my mouth and possible cancer which a doctor told me was a high likelihood when I had no money even to do tests (and this was actually something that contributed to my divorce FYI).
So yeah, a hard case, and yet with the opportunity to make more money I sold my fucking soul.

Everyone of my friends who has a college education meanwhile has a graduate degree and a double 6 figure income.
People not like me in my hard headedness but are like me in that they had a privileged upbringing but had to work for a living grew up with an entire different mentality: and that is that it is more mature to make as much money as you possibly can. Secondary is keeping your soul.
So think again about the landlord from the silent generation who has kids late so they are almost Gen X. Dies. And then their kids get their properties.

I've twice lived through exactly this situation in Oakland with different landlords.
I am Gen X. Many of us (without trustfunds but educations) learned that in an uncertain world plagued by austerity... that you need to fucking make as much money as you can, or at least compromise with the beast.

My second gen landlords of course had that thinking down pat.
So first situation. I move back to Oakland two decades ago to get serious with my girlfriend (now ex wife).

The landlords are old. Silent generation, lived through the depression folks. Rent is reasonable. Place is maintained.

I prefer SF but whatev. Compromise.
A year into renting this place - which happened to be on the edge of Temescal - (My ex did the photos celebrating the city's small biz loans that many including Bake Sale Betty got to start her biz then. we lived nearby.) - the old landlords are exhausted and hand job to kids.
So the very first thing the kid now managing the place for her parents says - we are going to have to raise the rent as much as possible. My folks have been way too lax, and generous.
Keep in mind, her folks managed multiple properties smoothly with reasonable rents. And they were well maintained. These were places that my ex (socially bougie to be fair) would agree to live in. I preferred lower rent. I was supporting us on piece work design and landscaping.
But the kids attitude immediately on inheriting properties which pulled in stable, sustaining incomes --- saw that her parents had foolishly not kept raising the rents to keep up with the market. The market was in a lull in 2004 too, but starting to heat up.
I want to really reinforce this, this kid saw it as a moral failing of her parents for not constantly maximizing rent even when the business was completely self-sustaining, and everything was well maintained.
Her older parents on the other hand even recognized this and warned us ahead of the transfer of management, that their daughter saw things differently than they do, had "different values."
Based on a reply I got above. I have oversold these people as boomers. These people were actually just a little bit older than boomers. Just barely in the silent generation, but significantly younger than my depression era grandparents.
So thats that. Not a horrible situation. I was not evicted on rent that was suddenly x3. I was just forced to deal with rising rent when the housing market was in a bit of a lull. And the landlord became colder. Less responsive.

But no threats of eviction. No rent x3.
So I moved from that place a bit after the rent went up because I was pissed. It was a one bedroom for like $1100 in 2004 and suddenly more with a promise of constantly more.

So I moved to the neighborhood I grew up in. A 2 bedroom for $1100.
Great neighborhood. Nice park. Library. Groceries. Good schools. And a few of the neighbors were clearly farming their .1 acre lots as much as possible. And some of my childhood friends still lived there in houses they inherited.
How did I land this gem? Luck. The place was run down, but livable. A couple units. I got the top. The landlord was ancient. He was an old black guy who worked his way up on the trains in west oakland, and managed to buy property from that work in ancient times. Very admirable.
We were good for years in this place. No rent increases. Reasonable maintenance done. But I was required to handle day to day shit for myself. A verbal requirement. Fine. I was living where I grew up and going to raise kids there. And not a techie. Good.
The guy was ancient but handled everything himself. A daughter was a property manager of other properties I think. And another daughter I knew nothing about. His son lived downstairs with his family. Let me talk about his son for a minute.
The son of the landlord and I did not get along. He hated the noise of my kids, and liked to throw loud parties to 1-2am. I waled into his party and asked him to turn down the music once. It never happened again, but he hated me forever after. Ranted all night about it on lawn.
Anyway, despite the antipathy we got to know each other, and his story is remarkable too. Unfortunately he died - but that is why I am telling the story. No one to hurt.
The son of the landlord was maybe 10 years+ older than me, but not much more. The youngest in his family. His father must have already been old when he was born. So he grew up through austerity when he was just starting his professional life.
His father was disappointed in him, so were his sisters. For reasons I won't share here. Anyway. He had to deal with a very successful and strong father who he couldn't meet the expectations of.
He did quite a few things included trying to get away from it all in Atlanta. I have heard the same story of many Oaklanders. Its like a sister city for many. Anyway he came back and in the 80's worked in the booming tech manufacturing industry.
Keep in mind that the Bay Area in the 80's had a booming sector which not only was good for people on the higher end but had a manufacturing component. (This was when all that farmland in Silicon Valley and Fremont got turned into office parks and light manufacturing).
So working in tech manufacturing was great for him. He made good money and had the opportunity to move up to more managerial type positions. Solid stuff. Well as well all know hat stuff got shipped the fuck out of here and most of those people lost their jobs.
As much as he and I did not get along, I admired him a great deal. He survived this total job loss and transitioned into running a janitorial business for the same office parks he used to make things in. This took time however. And didn't yield major success.
In fact it was only ever enough for him to live. He was someone on a track similar to an engineer on a manufacturing line (without the degree for it) and ended up hustling running a crew of janitors.
I dunno how that would affect you but if I had risen to a point where I was making the hottest new shit that was setting the world on fire to vaccuuming office park flowers and cleaning toilets I'd not be happy about how things worked out.
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