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. 

I know there are the obvious PITIA items but what about property management fees (I plan on using a property manager), maintenance/repair allowance, and vacancy allowance?

Obviously the ADUs are capped at 750 SF.My client and I are pursuing this option now! 

Market may not be ideal to sell right now, but if you wait as rates drop, you may get better pricing.If you do sell when you have no income, you obviously would be in a lower bracket.

Quote from @Alecia Loveless: @Randall Alan Obviously you can get close to the same return at the bank right now with a CD but you’re not getting an asset that’s being paid for by your tenants that will be worth several hundred thousand dollars one day, you’re getting no tax benefits, and your money is being eaten away by inflation.

Both of them have been great tenants but obviously can't live together with a protective order between them. 

Obviously smaller towns there, and I like to take a look at Zillow to get a gauge on the market for a future home. 

I do not like this as obviously if a business account is only accumulating rent from 1 property, it wouldn't accrue the cash in each as quickly as it would if all of the rents were funneled into one account.. and it makes paying the bills a bit of a pain on each of the properties as I am having things done to the properties, lawn care, etc.. constantly has me making owner investment deposits into each to cover initial expenses associated with the properties.. etc. 

Assuming your offer got accepted, the owner would need to get a unit vacated by closing (obviously this will need to be communicated).

I can’t believe how crappy some STRs that I have stayed in were, with obvious safety issues.