2 Years Into House Hacking a Duplex – Should I Keep It or Sell?

Question

I'm looking for some advice from people who have experience with house hacking or owning small multifamily properties.

I bought my house in March 2024 for $290k with about 5% down. It's a duplex now, but it was originally a single-family home. I live in the downstairs unit and rent the upstairs for $875/month. My monthly payment is around $2,500.

When I bought it, my plan was to house hack for a few years, eventually move out, rent my unit, and keep the property as a long-term investment.

The problem is that after almost 2.5 years, I'm realizing the property has more issues than I originally expected. I've probably put around $12k into maintenance/repairs already, and there are still some major things I'm dealing with:

• The roof may need significant repairs or replacement.
• Water still comes into the basement during heavy rain.
• There has been some water damage from the upstairs unit.
• I still need to replace the washer and dryer in my unit.
• There are other smaller repairs that keep coming up.
• The layout is also pretty awkward because of the way the original single-family house was converted into a duplex.

I estimate the house is currently worth around $320k–$325k, so I do have some equity.

The bigger issue is that I don't really like the house anymore. There are certain things about the structure and layout that I never really liked, and my fiancé doesn't like it either. We're getting to the point where we don't want to live here long-term.

So now I'm trying to figure out whether I'm being too emotional about the property or whether this is a sign that I should move on.

I'm considering:

• Keep it and put the money into it, then eventually move out and rent both units.
• Do only the necessary repairs and hold it as a rental.
• Sell it and take the equity, then move on.
• Sell it and use the money toward a better investment property that I'd actually want to own long-term.

I'm having a hard time figuring out where the line is between "this is just part of owning real estate" and "I bought the wrong property."

If you were in my position, how would you approach this?

Would you look strictly at the numbers, or would the fact that I don't enjoy living there and my fiancé doesn't like it be enough of a reason to consider selling?

What numbers would you look at to make the decision?

Also, if there are any local investors in South Jersey/Philadelphia who have experience with duplexes or house hacking, I'd be happy to buy you a coffee and meet up. I'd really appreciate talking through the situation with someone who has experience in this and can give me an outside perspective.

Thanks in advance. I'm really just trying to figure out whether I should keep working on this property or accept that it may be time to move on.

Wale Lawal · Answer

@Sayghim Kuay

I would back off and try to view the property as though I was buying it today. Determine how much it will really cost to replace the roof and fix the water problems as well as any other necessary repairs and then compare this cost with what you can do with the amount of money you will make selling.

Good luck!

Richard F. · Answer

The first question...is it a LEGAL duplex, in terms of zoning and per building codes? If yes, then by now you should have a complete list of repairs and improvements needed over at least the next 3 years. Prioritize them. Water related issues are destroying the structure, so they need to be dealt with first. Water intrusion into the basement should be pretty straightforward to address from the exterior. Leaks from the unit above certainly need to be resolved, as the hidden damage can be extensive. Both of these water issues make the lower level unrentable. Roof, depending on actual condition, may have options for shorter term, if you can't do it right. Have you obtained legit estimates for any of these issues?

Michael Eskenasy · Answer

We’d separate this into two decisions that are getting mixed together:

• Do we want to live here anymore?
• Would we buy this property today as an investment at its current value, condition, debt, and expected rents?

Those are not the same question.

For the investment side, we’d keep a rolling record of the property rather than looking at the original $290K purchase decision. Current value, remaining loan balance, realistic rent for both units, vacancy, taxes, insurance, maintenance, capital reserves, roof/basement work, and the opportunity cost of the equity all get updated.

Then we query the property as it exists today.

The question becomes:

If we had roughly $30K+ of equity sitting in cash today, would we choose to put it into this duplex, plus whatever additional capital the roof/water issues require, for the return we expect from both units?

If yes, keep it.

If no, selling isn’t admitting the original purchase was wrong. It’s reallocating capital because the current version of the deal no longer wins against the alternatives.

I’d also put a real number on the deferred work before deciding. Roof + water intrusion can turn “I’ve already spent $12K” into sunk-cost thinking very quickly.

And I wouldn’t completely dismiss the personal side. If you and your fiancé both dislike living there, that has a real cost too. A house hack is supposed to improve your financial position, not require you to indefinitely tolerate a property you both hate.

We’d make the decision from the current state and forward return, not from what we originally hoped the property would become.

Joseph Zimmerman · Answer

I run my custom P&L on each of my two Chicago rentals every month, with repairs and capital items on separate lines. Because I self-manage both from out of state, how I feel about either building never enters the math. My condo's assessment absorbs the building systems, so its repairs line is only what happens inside the unit. My house carries the roof.

You've got 30 months of actuals on this place. The $12k is roughly $400 a month in repairs. Price the roof separately as capital, then run both units at market rent against that total.

Hayden Gray · Answer

I'd recommend finding a trusty handyman to help mitigate some of the water damage items. Get estimates and use data to drive your decision making. You don't have to live in the house to keep it

Aaron Zimmerman · Answer

How much can you rent the side you live on when you move out?

2 Years Into House Hacking a Duplex – Should I Keep It or Sell?

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