@James Mays In my market there’s usually little to no negotiation on repairs found in the inspection.

@Ron Dancy in some ways yes, in other ways, no.

I'm looking to start off in areas with lower costs coming in, preferably under $100k single families but definitely under $200k. 

Guests treat those kinds of bookings differently than a STR vacation home.They are used to being able to cancel the booking 24 hours in advance and all sorts of other things that STRs like ours can't really accommodate.

We are currently looking to invest in Wisconsin.

We use this in our personal flip and rental business and also in my bookkeeping business with other clients.  

I think your best approach is to pretend you are the investor yourself, calculate build cost (mortgage with interest) + Maint / cap expenses/ management fees according to your zoning and then compare that to the average rent in that neighborhood.

How do they get tenants in place, and how difficult is it really?

The answer to your question may be in your lease.

Just the actual cash value   You may want to find a good broker in your area that works with real estate investors.