I used to have a two bedroom apartment that I lived in and I would rent out the second room on Airbnb and one time I got a guest and she would leave her windows open.

A few other things I'm considering;- I don't need the extra cash flow to live and am just approaching it to remove the high mortgage interest, but also hedge risk that the current stocks might tank in a few years.- Could take all current cash flow and a few thousand a year to pay off the property in 5-10 years.- Hold for a bit and 1031 into something else but am fairly confident there is not much appreciation to come on this property.

Hey @Jerry Nogueras - I was in your shoes too, born in NYC, and lived between there and Long Island. 

Where you live in relation to the investment property shouldn't matter.

Now the living room and 2 bedrooms that just had new flooring put in them 8 months ago are ruined from the leaking water from the HVAC and have to be replaced again.

I would love to hear any suggestions about where I should look to live in the area. 

I already make a living out of real estate and I'm not planning on ever leaving this space, I'm here to stay. 

I have friends who have  LTR/STR and MTR is where I live.

I would like to get the names of non-profits in MD that run sober-living homes.

I feel like I've dealt with every time crazy situation there is here in Chicago with squatters, evictions, drug dealers, etc., and I still love Cook County because I have a solid team and underwrite deals properly.I think @Paul De Luca nailed it on the head, though - it seems like you are quite risk-adverse, so maybe given your risk tolerance, it's not the best idea, but if it were me, I would not think twice about it, and find a rock start property manager who knows exactly how to vet tenants.