I want to be somewhat hands on so I would pick markets that are driveable for you and visit frequently. 

Then determine if you have and are willing to risk the necessary capital, time, and commitment.3.

Cash for keys is common, and frequently the part that keeps tenants from moving forward is not having an affordable place to go to.

He frequently works with STR investors in the Smokies  River - thanks for the referral.

The first thing I'd recommend is focus on a market where you either 1) currently or have previously lived, 2) have family/friends that live there, or 3) travel to/vacation there frequently.

Hi @Tim Holt I think in general house hacking is usually a good move because it gets you off the sidelines and into the game with the most favorable financing possible (30 year fixed).There's a lot of value in getting started today vs waiting some undefined number of years until conditions are better, which could be a long time from now, because real estate is a business and the sooner you start actually learning about that business, the better.With all that said, I always recommend that people analyze any potential house hack as a pure investment that they aren't going to live in, because someday they may want to move out and you should know up front (before you commit) whether you're going to be able to do that, or whether you're overpaying and will be stuck in the property unable to move out because it'll be cash flow negative if you do.So you had it exactly right when you wrote, "the property would need to cash flow when I move out and rent out all units."

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However, fact patterns are frequently similar and and become easier to resolve (or run away from).The property is subject to competing spousal claims.

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I would not make this a legal matter, but you will have to decide if you want to commit to living with this landlord.