One thing people constantly ask me is, “Hey Josh, what’s it like fixing up an old house in New Haven?”

To which I reply, “Excuse me what?”

Nick Young Confused Meme

In reality, I’d say it’s less that I’m fixing up an old house and more that me and old house are watching each other decay.

Purchasing a house is an enormous life decision you should absolutely put in the hands of someone who runs a blog.

Should it be in New Haven? Let’s check the stats!

Pro: You Don’t Have to Deal with Shitty Landlords Anymore

Chances are, if you’ve lived paid rent in New Haven, you’ve dealt with one (or let’s face it, many) terrible landlords.

Some of them are faceless corporations preying on the desperation of time-limited Yale students. Some are absentee slumlords with shell corporation LLC’s who seem determined to let entropy take their properties.

Run Down House in Detroit
Affordable apartment in East Rock, probably

When I lived in the Strangest Apartment Building Ever, during very heavy rainstorms, the ceiling would leak water. I’d be putting out pots and pans like some kind of real-life Donald Duck.

They just… never fixed it.

And PMC isn’t even close to the worst landlord in New Haven. (Congrats to Mandy/Pike for their continued innovation in this field).

Con: You Are Now Your Own Shitty Landlord

It turns out fixing stuff is actually pretty hard. I don’t know about you, but I’m actually not qualified to be a handyman at all.


My first year of home ownership I was like okay I am gonna fix this house up and make it a warm, wonderful place I can invite my friends and family! I’ll paint the doors and fix the drafts and buy nice rugs and add beautiful new light fixtures.

Now? I’m like okay well that sink works at least 8 months of the year and that’s pretty good actually. I mean, how many sinks do I even need? Like one?

Sink Required Per Household Graph
Source: Science

Shit is gonna break. And you’re gonna freak out. And then eventually, you’ll get so used to shit breaking that you’ll be like… eh… whatever.

Also, you have to like… take care of stuff. Like mowing your lawn. And oh my god the leaves. Why do trees have so many leaves?!

Pro: You Can Have Your Own Outside

When you live in an apartment building, if you want to go outside, the only available green spaces are typically community areas like New Haven Green, Wooster Square Park, that Tiny Sad Piece of Grass In your Apartment Building Courtyard, etc.

Trocaire College Courtyard
Enjoy Your Allotted Nature, Humans
Source: Emily Burns [CC BY-SA 4.0 (]
The first time I sat down in my own backyard on a warm summer afternoon with my laptop, writing terrible jokes without anybody to tell me about this Jesus fella?


Being able to have your own little quiet area is… pretty rad.

Con: Other People Also Have Outsides

Did you know some people have children? Just running about? Sometimes those same fools are your neighbors. Just twenty feet away.

Also one of my neighbors seems to spend like 70% of his time cutting metal? I don’t really understand what kind of business model or personal hobby or whatever is going on.

Simpsons Anvil Steelworkers Club
My neighbors apparently

Con: Your Taxes Might Suddenly Go Up 11%

When I was first figuring out how the mortgage payments work, I was trying to figure out why the bank needed some large escrow account. After all, if I was paying my bills on time, why do I need extra money for “in case”?

They basically were like, “listen, your taxes are going to go up at some point, and when they do, you’re suddenly going to owe a bunch more money, and it’s a lot easier if there’s an account that we can spread out that damage to.”

Oh. Cool.


So yeah your taxes might suddenly go up 11% and then the Mayor is like “Hey life’s tough all around I don’t know why you wouldn’t re-elect me look at all these fancy-ass new apartment buildings from people who probable aren’t paying taxes anyway”

Pros: You Were Already Paying Those Taxes

Renters think they’re so funny when they’re like “Oh I’d never buy a house in New Haven, the taxes are way too high.” They smirk, raising their eyebrows at me. So smug.

Smug ceramic pig
You think you’re better than me because you don’t pay taxes, ceramic pig?!

Except you’re already paying taxes. What do you think your rent is. You think your landlord is like “Oh I’m just gonna charge them for the physical structure they stay in, and if I lose money on taxes well that’s on me I guess.”

Nah your rent already has taxes built in.

Pie Graph of Rent Costs
I think I’m only going to do chart-based humor from here on out.

Con: Lack of Freedom

When you rent, you can always just… leave. Well, at the end of your lease. But still. You are relatively free to come and go.

Job got you down? Relationship not working out? Feeling stuck in the same old life?

Surely running from your problems by going to a new location will help!

Me? Let’s say I want to go pursue comedy in NYC because I don’t hate myself enough here.

Well I got this house. And I actually owe quite a bit of money still on it, even two years into a 30 year mortgage! So I’d have to somehow sell it at a profit.

I know you’ve heard a lot about Gentrification and all that, but I can promise you, we are so far from having a muffin shop in Edgewood. We’re much, much closer to having some kind of Loosey Superstore.

Pros: You Meet A Lot of New People

Chances are, unless you have a cool $750,000 lying around to buy a house in East Rock, you’ll probably end up in a different neighborhood with totally different neighbors than when you rented.

Being in Edgewood, I gotta say this is definitely the widest different variety of humans at totally different stages/backgrounds of their lives than I’ve ever lived around. We’ve got retirees and young parents and starving artists and people who seem to drink professionally on their porches. The whole gamut.

Walkers Chips
There are basically five types of humans/chips

And I absolutely think it enriches your life to meet as many different types of people as possible. Because they’ve got the good drugs.

Pro: You’re In on New Haven

If you buy a house in New Haven, you absolutely give a shit about New Haven. You are invested.

You’ll start attending local meetings with your Alders. Making comments on the New Haven Independent. 😉

You keep getting out there and playing your cards right, you just might end up on my podcast.

One of the best things about New Haven is that as a small city, there’s a really tightly-knit group of people who are trying to make things happen. When you are a part of that group, you get to know your peers and their passions and it really makes you feel connected to the community in a tangible way.

You care about your neighbors and your block and you want everyone’s lives to be getting better. Sort of a… reverse Yale.

Should You Do It?

I don’t know!

In reality, it depends. If you have the money, and you think you’ll be here for at least 5 years, and you’re up for the additional labor you will definitely be stuck doing. Like yard work. Ugh.

If you aren’t sure, then you’re probably better off living in one of the 55 new “market rate” apartment buildings popping up around the city and living in your beautiful little palace with ping pong tables and rooftop singles mixers.


We Want Writers!

As much as I love the sound of my own voice, Between Two Rocks is, ideally, for other perspectives and views on the city.

Do you have an opinion? Great. You’re qualified.

Uncle Sam
I apologize for the hack presentation.

I’m looking for people to contribute on a one-time or repeated basis.

And get this. I’ll pay you $20 for an article. That’s right. Twenty bucks. For writing your opinion.

What do you have to lose?

Email me at and pitch me your ideas!



One Comment

  1. The tenant can also become the landlord and earn and capitalize while moreso enjoying homeownership in a great urban place. Plus you could be a proactive landlord updating stuff ahead of time and keeping a good nice place for your tenants. Plus you can also provide a place without charging the maximum rent possible.. The tenant may even come to like you and stay with you for 20 years saving you down time every few years with the apartment.

    I’ve been a landlord and homeowner in New Haven many years. The city can empower you.

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