. :)There are ways you can craft this deal to work for both of you -- I think the biggest thing is adjustment to the purchase price to accommodate the rent difference or "good deal" you're giving him.

Whatever the decision, make sure you adhere to fair housing laws as well as local ordinances.Best approach is to craft a list of criteria and treat everyone the same.

You'll feel a lot more confident talking to clients if you have a good understanding of the process from start to finish. also, be a master at your craft. sounds like you're already finding ways to emerse yourself in the industry. there are a lot of "professionals" who know nothing and talk as if they do. dont be one of those guys :) check your ego at the door, and understand this industry is always evolving. you will continue to learn 10 years in, 20 years in, 50 years in. 

There are 3 ingredients to a successful direct mail campaign:1) A highly targeted motivated seller mailing list (absentee, probate, pre-foreclosures are some examples);2) A well crafted letter that appeals to your motivated seller and makes that seller call you; and3) A follow up system (send several letters and when they call and if they've shown some motivation, follow them up until they sell their house to you or someone else)The above is what happened and what I've learned in my real estate business.

Has anyone ever rented a property to individual trade market booths (i.e. crafts, boutique shops, etc)?

The area I live in is also becoming known for the multiple craft breweries. 

Our closest one to Boston is in Waltham at the craft food hall and the Lowell meetup is our biggest.

Are you looking for individual crafts or a GC?

Well crafted.

In that time you could establish relationships and focus on your craft as an investor.