(This is someone who knows what I can do and trusts me to do what I say I'm going to do, however I want to be professional in every aspect)Should I seek an attorney to draw one up for this agreement?

You keep the deposit as he failed to follow through, then start marketing your house or find a realtor to sell it-don't trust wholesalers.

@Kathy Green Hard money lenders won't lend on a personal home, trust me.

If he has been doing it his way for almost 50 years there is a good chance he isn’t going to was to hear it frankly.That said, if you play along, even if you can’t use subtle techniques to move things along, you may win his trust and be given some buildings to manage- after which you can slowly change things.Above all else enjoy your time with him.

I never trust tenants to give me good info on previous LL's after I escaped a scam someone tried to run on me.), etc.

But the name of the game is skate to where the puck is going....this market seems to have a vibe of affordable housing, space, yard, single family, etc... in my opinion Not sure about NY, but Cleveland has pockets of massive appreciation.Tremont, Lakewood, Ohio city - all neighborhoods of 2x-4x appreciation over 7-10 year horizon..... not sure now as I never had the stomach for the risk/reward.I always operate in the same market since I’m a high velocity flipper and deals exist all over the Midwest key is building relationships and trust in your market.

List Your PropertyApproved listings are displayed on both of our sites:  Trusted by over 40,000 property owners Average length of stay is 92 daysOver 2 million searches a year by healthcare travelers, medical staffing coordinators and other corporate travelers looking for monthly furnished rentals

You can DM me and I can give you some people that I trust, and I know will do a good job even if you are out of town. 

@Julie K Fredrick never completely trust the advice of someone whose salary depends on the outcome, no matter how well intentioned (ahem).

Trust me, I have learned that the hard way.