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Real estate missteps: Should I give up on trying to be a homeowner?

Post-divorce, I have attempted home ownership three times, and while the decisions seemed right in the moment, in retrospect, they feel like missteps.

- I did a cash-out refinance on 1960s marital home, but maintenance and repairs were too expensive/overwhelming.

- I bought a 20-year-old townhome, which ended up needing HVAC, AC, and water heater replaced in the first six months, followed by HOA special assessment for new roof. Not having enough natural light and a yard for kids was also tough.

- I bought a new construction single-family home, but the payment is now $500 more a month than it was at closing due to increases in taxes and HOA. Half of my take-home income (FT job plus side hustle) goes to mortgage/HOA payments. I'm worried this is unsustainable once the home starts needing repairs, given my other expenses as a single parent.

Do I:
- Try to stay put, even though I am living paycheck-to-paycheck?
- Sell (currently buyer's market in my state) and try to buy something with a lower monthly payment (i.e., probably looking at an older townhome again)?
- Sell and give up on home ownership and rent? (Why does renting feel like a failure?)

No need to chastise me for my real estate mistakes. I've already beaten myself up enough.

submitted by /u/misfitmpls
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source https://www.reddit.com/r/RealEstate/comments/1pumq0j/real_estate_missteps_should_i_give_up_on_trying/
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