If I were in a better financial position right now, I would definitely start getting involved in real estate by investing with an owner-occupied MFH and go from there. 

Every deal we do involves skip tracing and cold calling.  

Also, I want to add, if you're putting together a proposal or even an OM, then I would add the risks involved with investing.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

The idea being I am more involved than a strict turn-key and am able to reap some equity from the start.

I would hire the right contractor that is missing a leg, an eye and 2 fingers, but this guy doesn't sound like a contractor, he sounds like the guy "living in a van, down by the river" (or in this case a boat).

I want to help him out and buy the property at the same time but not sure of a good way to do this without the wife's involvement.

@Anna Brent, You get a property under contract that currently is involved in a suit for back taxes. 

Fact is you should not be getting personally involved in your tenants lives. 

To many variables involved and without any guidance will cost you dearly.