@Luke Davis If you can qualify for a conventional loan that is probably going to be your best bet.

Housing prices in Beloit are definitely cheaper than Janesville, and Janesville is (for obvious reasons) significantly cheaper to invest in than Madison.Can't be of help to the property management part though... we've looked and looked but haven't found a company we are comfortable with... your best bet there would be to join up with the Southern Wisconsin Landlords Association and network for a quick recommendation. 

If you position yourself on the outer edge of that moving path of progress, there could be opportunities for STR/MTR/LTR all in the same neighborhood, which gives you that desired strong pivot-ability.  

The best bet is to find an insurance BROKER (keyword) and have them search around for the best rate to see if they can beat any of the three I named. 

There are several things you can look into @Nicholas Cavato, but you have to do the legwork.Having said that, I am betting that they will not be lifting any restrictions or caps anytime soon.

Best bet would be to talk to an investor friendly lender. 

I didn't expect the floors to be as good as new but I did expect there to be a stop in the progression of the problem.

Richard Helppie-Schmieder Group Saturday mornings 2x month at 8am sometimes in Carrollton, sometimes at projects in progress.

It’s a SFH and I don’t rent it by the room, but I bet State Farm wouldn’t have a problem with it on this type of policy.I ended up with this policy after searching almost 6 months for someone who would cover an STR in a high wildfire risk area.  

When flipping there's many things that can come up out of your control that can prolong your progress and therefore your investors might begin to get impatient with getting their return.