If you enter the auction game you need to be in a position to walk-away and forfeit that deposit if during your due diligence you find out that the property is going to be a dog.

Don't skip the process in vetting this person, and be sure you can deliver; if not, he will play the "blame game."

Attempting to time the market is a losing game - that goes for stocks and it goes with homes.

Starting with a single family is great if it gets you in the game. 

I am in the buy and hold game, but sometimes flips make more sense in order to generate more capital.  

I would make ZERO OFFERS until you have a game plan and run the numbers on the prospective property.

MA has very tenant friendly laws and people can try to game the system as much a possible, I've heard some horror stories from friends of friends about bad tenants that were able to stay in an apartment for over a year WITHOUT PAYING RENT!

But yes, the time game in this case, he may still want to dump the house sooner than later! 

Playing the long game in a stable market is smart.

But then the end game with the equity kicker is the icing on the cake.