Love th idea of real estate investing but isn't brrr strategy very dangerous of tenants stop paying rent.

Do not invest in any city on Neighborhood Scouts’ list of the 100 most dangerous US cities.✅ Low risk of a natural disaster: The issue isn't your property.

Collecting rent in this area is downright dangerous.

As others have said, I would generally avoid HOAs completely unless you have the time to research each specific community.Your best best to is to buy a place in an up and coming area (read somewhat poor, but not dangerous) and plan to hold.

You're getting into debt financed distribution territory in your latest post, which generally increases the amount of work your CPA needs to do and therefore your fee.If you can't speak to your CPA without him or her charging you hundreds of dollars, or if your CPA can't convey concepts and holistically advantageous paths forward to you, you should probably look for a new CPA.You shouldn't have to learn tax law and strategy just to talk to your CPA. 

Out of state deals are fraught with danger and I always recommend restraint when doing so.

So yep, turns out, I needed to sell by July 2023 to claim the capital gains exemption.So now that I've missed that boat, my options:Continue renting as is and make about $9K a year but let the renter pay the mortgage (will still have to spend $10K on a generator)Increase the rent and get to $15K a year and let renter pay the mortgage (will still have to spend $10K on a generator)Spend about $100K building an ADU, pay an additional $10K to add a generator (we live in hurricane territory) increase the main house rent and get a second property but now have an additional $100K payback for the ADUSell, pocket the approx. $315 and get about $15K on all the current 5.5% savings accounts.The latter seems to be the most attractive. 

Unfortunately, this will almost certainly be a second-position loan and as dangerous as they come.

In addition to the flaws in the cash flow logic Twana Rasoul points out above, you also run into the danger of overpaying for your "turnkey" (turkey?)

I am a wholesaler and New Haven County is my main territory.