Most tenants, when receiving a check in the mail are going to cash it.

Offer to give him a slight discount if he stays, certainly no more than 10% below market.

You can read more about this tax at www.IRS.gov Pub 598.

THANKS in advance for recommendations!

First purchase story with first 6 months no mortgage or rent is detailed in Bigger Pockets Podcast #82.

Lease Agreement: Use a compliant, detailed lease covering rent, rules, and responsibilities.2.

What's the breakdown in tenancy between the shops and any income from the barn (or the house)? 

I don't think housing will be any more affordable for the next few years than it is now.

@Josh LemonsThey have a regulation A offering which is open to accredited and non accredited investorsThe great thing is they have to submit their offering circular and have it qualified by SEC as well as submit financial information etc.All this means is the information is readily available and if you do not understand it then I recommend engaging an attorney who can interpret it.

I wouldn't say that people in general like one type over another, but rather people in general cohorts (single, married - no kids, married - with kids, etc.) tend to gravitate towards certain types of properties based on their lifestyles.