If he is not licenced/insured, friend or not, you do not hire him.Precedents dictate proper professional management of your business.

Once you have vetted the operator and find a project you like you can leverage the experience of a real estate professional to run the day to day operations. 

He can explain land trusts pretty well and has first-hand experience using them, but he is not a legal professional. 

A bit of advice to new agents and aspiring real estate professionals, FIND A MENTOR WHOM YOU ASPIRE TO BE LIKE, FIND A FEW SO THAT YOU GAIN MANY DIFFERENT PERSPECTIVES ON THE PROCESS THAT THEY TOOK TO BECOME SUCCESS.

Recommend professional evaluation and repair which may include perimeter drainage and sump pump, sealing the gaps around the main drain, and adding New Vapor barrier and insulation.

(*Relatively high compared to what we see from "professional" management companies and compared to most of what else is available in the sandboxes where we play).

Readers are advised to seek professional advice.

These are professionals with additional training and a stricter code of ethics.

My tenant (single professional) has occupied the home for a full 2 years now.

Be a sponge and take notes.Third, consider joining a local real estate investment club in your area to network with other real estate investors and professionals locally.Finally, bring your deals here so the more experienced investors can help you get your deals done right.Happy to help in any way I can.