I'm self employed since 2014.  

He hired dedicated guys that do our jobs and our business pays their exact wages plus comp and some small expenses around keeping them employed.

Hi @John Ibbits, and congrats on recognizing the value of real estate as a wealth generation engine. 

If we have a unit that can generate close to market value rent, but is not updated or a place we would want to live in ourselves then we have to consider the quality of resident that will live there.

Main items of concern:Lease set up: Business to owner, specific items to include - boiler plate or company that can generate for a feeLiability issues and insuranceADA requirements: the owner had stated only required depending on what tenants live in the facility- carbon/smoke alarms - no ramps, etc (seems fishy as in construction rules on ADA are stringent)As the owner do I need any short of license?

BTW, we love this market because we've got a major university a few blocks away, Fortune 500 employers in the area and other factors which drive constant rental demand.

Or alternatively your agent can connect you with a lender that offers a special product like a rehab loan (not all do) or is better with underwriting self employed individuals.

I live in Oregon and have a long term rental in Central Texas that I'm considering flipping over to Airbnb to generate some more income, and so that when I'm in Texas I can stay there, saving me money.

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We lost his money on one, and while it didn't hurt the family dynamic, my wife and I hear about it from time to time (the latest being that he is still burning through his losses on his taxes, since he doesn't have enough passive income/gains to use the whole loss yet).Stories I have heard: there are families that have been completely decimated by going into business together, and there are families that have run successful multi-generational businesses.