Its important to know what the max rents will be so that you can cover your mortgage payment and hopefully also cash flow every month.

But that also depends on your down payment- putting only around 20-25% down is hard to have a profitable STVR.Ultimately with STR v LTR, I'd be mainly curious about your intended use of the property. 

I would just take into account that a lower down payment will mean a higher monthly payment so be sure to run the numbers conservatively in order to ensure your STR revenue is able to carry your monthly payment with this higher mortgage cost. 

There is no issue with eviction for non-payment of rent during the winter in Wisconsin.

We have numerous who have their payments set up to auto-pay.

Run the numbers as if you leased the property from him at 10% x the value of the home( not including 1,000 acres) in lease payments @60% occupancy.

I had to borrow the down payment form my parents because I was BROKE. 

Yes, my banks require a 1.2 DSCR debt service coverage ratio, meaning they want to see rent 20% higher than the mortgage payment.

The biggest factor is thoroughly review their credit score report especially on time payment record and score.

Work on getting a down payment saved up while managing your townhomes.