It all seems to work out for everyone.

Find a solid contractor(s) and realize that the "deals" with people in exchange for work almost never work out unless they are ALSO paying holding costs...otherwise, they just do it when they want and often that is AFTER everything else.2.

You would not be able to lend him money in this case.But maybe something can work out where he creates a Qualified Opportunity Fund where you are both partners and it is funded with the proceeds of the sale of your second home. 

If this deal doesn't work out - Don't give up...My suggestion is to locate an operator/sponsor who has the experience you seek.

I tried this with another friend and made the mistake of making him an equal and trying to do deals together splitting it 50/50 and it totally did not work out.

What are you trying to work out regarding the area?

For a number of reasons it would work out better for me to purchase the property myself first. 

We're doing a RTO situation which should work out nice.

I started my legal career in 2002 representing WFB on their commercial workouts, note dispositions and commercial collections in State and Federal Bankruptcy Courts and after a few years moved over to representing Albertsons in various commercial real estate matters and mergers and acquisitions. 

Then, on to the next unit...Inherited tenants almost never work out, in my experience.