@Heidi FahringerReal Estate Expertise - Are they familiar with real estate-specific tax strategies, such as depreciation, 1031 exchanges, and write-offs for repairs, property management, etc.?

I'm aware of the challenges and I am welcoming to them in exchange for the experience of helping sellers solve whatever problem that they might have.

Most criminals defrauded the IRSI wonder what would happen if the people who combined lost like $2M all sent 1099's to him-I bet that would wake up the IRS but not sure if it would impact their claim later on.

Especially with the favorable tax incentives offered to buy and hold real estate vs the ordinary income tax you'll pay on private lending.A 1031 exchange would allow you to indefinitely defer all of the capital gains tax you would have to pay, and instead use it to purchase better performing property/properties.

I'm considering selling my rental property in Atlanta to buy additional properties in the Pittsburgh PA area (using 1031 Exchange). 

I bet there are some ways you could proactively plan so the problem almost resolves itself. 

I think your thesis is sound in general, but I would want a hedge on my bet.

I imagine you'll have the same issue with the unpermitted kitchenetteIf you can rent the property as a MTR then listing on Furnished Finder will probably be your best bet.

You bet, but not active or pre-foreclosure.

Your best bet would be to hire a good property manager who screens well and knows what they're doing and you should be able to get good income over a few years.