Hmmm that is nearly 5 years backlog if NO new homeowners miss any payments.But in real estate investing, Short Sales only need "1 house payment" missed.

I bought the house in December 2022 to start a short term rental.

Your home insurance might allow for short term rental use with an endorsement but you'll have to discuss with your agent. 

A property owner may not seek a permit for a SB 9 Two Unit Development during the 15-year period after RSO units have been demolished or withdrawn from the rental housing market (Ellis Act).

I think they're referring to Short Term Rentals (airbnbs, VRBOs, and such). 

You also need to figure in the holding period of the properties and how quickly you plan to exit, those should weigh in the calculation as well.

understand the negativity here.The way I see it, the DST niche is for real estate investors looking to leave property ownership behind and "cash out" by deferring capital gains until the holding period is over (assuming you don't 1031 into another).

The intentions were to buy a 2nd property within 2-3 years and then use this home as long, medium or short term rental.

Long story short, he wants to build a new home that would serve as his primary on the 5 acre lot. 

It seems to me that the 21-day period in Wisconsin is half-baked, given that water is a utility that often runs with a property and not the lease term.