This tax tidbit was updated just a few days ago and says: "There is a special rule if you use a dwelling as a home and rent it for fewer than 15 days.

And if something bad goes down, like the other dwellings need to be pulled, you can walk away from the deal.This really is stuff your real estate agent should be telling you.

That's why I mentioned a TIC in a Trust.Actually, Steve has some other problems here that should be addressed first.6 houses on 6 acres, that is not the best land use, the utility is limited which effects the marketability, the "ease of transfer" of title.Each house will be worth much more sitting on its own lot instead of on "shared grounds", the land value isn't there for each dwelling. 

Insurance companies do not want you to cash out and buy a new property because it will leave them holding onto a burned or damaged dwelling and empty lot to deal with.

Have you ever looked into adding a garage apt / accessory dwelling unit where a historic garage once stood?  

This much work is going to require building permits, and most of it will require a "Dwelling Contractor License" from the State of Wisconsin. 

If I were you I would strictly look into out of area multi family dwellings. 

The city of Grand Junction and our county have generous rules regarding "ADUs" (accessory dwelling unit).

Seeing as this is the New Construction forum and a lot of the questions are some version of “how much does it cost to build X” I thought I would share some real numbers and experience from a project we currently have under construction.This project is an Accessory Dwelling - 720 sqft with one bedroom, one bathroom, a living room, kitchen and small laundry room plus a screened porch.

(a) A landlord shall disclose to a tenant, or to any government official or employee acting in an official capacity, according to this subchapter:(1) the name and either a street or post office box address of the holder of record title, according to the deed records in the county clerk's office, of the dwelling rented by the tenant or inquired about by the government official or employee acting in an official capacity; and