@Ted Strzelecki interesting about the tax/modelling regulations, I did notice another BP member from the same area call it the state of Tax-achussets, so I'll look into that.

What I think he should look into, is establishing a contracting business LLC, opening up a solo 401k, rolling his IRA into that, and then investing in rental properties.  

It's important to stay compliant with RESPA and other regulations and that's part of the servicers job. 

I'd be happy to give any suggestions to help but real estate is local and there may be rules or regulations that may make some of these suggestions unavailable in your area...

There are a lot of buyers, especially younger buyers, that want a new, modern, never been lived in home, in an established neighborhood. 

Remember this, anyone that has to go to school, pass a state board, then take more courses to keep a license and keep furthering their education because Real Estate for anyone with a license is regulated.

However, if they had a 10 year credit history and on year 7, 8, and 9 had a credit slump due to a long job gap and after they got their new job have re-established their credit, then I would take a chance with them. 

Once you hold the deed to the property you have now established a vehicle to cloud the title. 

You could try to get a low maintenance ground cover established in the areas that get weedy.

There are of course the rules and regulations of getting a broker license, off the top of my head I do not recall but I believe it's 2+ years experience and/or a certain number of transactions under your belt.