The window concern almost broke by heart, as the winters here in Wisconsin got to -38F this past winter.

I could move into a property that looks like a good deal (either in SF or the Easy Bay) and secure an FHA for 3.5% down by virtue of living in the property as my primary, rent out additional rooms, and essentially function as the property manager.

Conrad, look up Brew City REI Club if you are interested in participating--it is a private, give and take, invitation only real estate club of active local investors obsessed with real estate in Wisconsin and charitable in helping each other succeed.  

I'm looking for someone in the Fox Valley, WI area to learn from.

The one that is leaving wants his security deposit back.

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

If a tenant gets a protection order, I'd change out the locks and probably install a security camera.

Trying to avoid neighborhoods that would require me to hire security for a property, but I don't mind taking some risk.

Would finding a wholesaler to secure deals for me be counterproductive?

Insurance costs will go up when your value goes up, obviously and the bank will likely make you secure a year of premium before refinancing.