I am seeking opinions from experienced RE investors and/or landlords.  

I'm  in my early 30s, and an experienced software developer currently looking for passive income opportunities, but I would like to eventually move into real estate investment full time when I get into my forties. 

I would love to trade real estate secrets for some insurance market advice.

I'm sure there are ways to structure the lease to take these things into account so I'll let the more experienced members speak to that, but I would personally be very wary. 

A better route might be to put up some cash and partner with an experienced investor in the area.  

If I were you, I would take my money, get some free education (Bigger Pockets podcasts & Beginners guide) and find some one experienced to learn from.

I am curious what others have experienced with tenant demand in winter in the upper mid-west.

The very experienced Mr @Bob Bowling said ..."

Most people with any experience will see through your facade if you try to portray yourself as experienced when you are not.You are more likely to get taken advantage of then because you will not be able to ask appropriate questions without blowing your cover.

Remodels ALWAYS have unforeseen issues, even for experienced contractors.