If one is a duplex and the other a single family home...I'd bet the single family home is the better one to sell. 

But, I would not bet on a boom in rents or prices until 2026 at least. 

For hardwood, that will take much longer and I'd bet they'd walk on it or move heavy furniture before the top coat is cured and damage it.

The best bet is to take this commercial. 

@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. 

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. 

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.