At the next lease signing you may want to consider doing things differently.

Your lease terms will also have to be at least a 1-year term, as Freddie mac will not utilize month-to month tenant at will terms if you want to use that income for newer property owned less than 1 year 

Purchase the lease from the Wisconsin Legal Blank website.

The building is worth really close to that (based on my realtors guess and my own research / knowledge of the area).I was thinking of offering the seller a Lease Option where I lease for ~3 years then purchase.

Currently both properties are leased by that amount.

The option that I see in achieving my goal is first, trying to use Airbnb get more cash flow on the first house as soon as the current lease expires (since the property cannot be rented more that the current amount).

The other issues I can see is the fact that he has just a verbal month to month lease.

Some will charge a percentage each month but also a start-up fee, a leasing fee or lease renewal fee each year, administrative fees, maintenance fees, etc.

The lease with our renters is coming to an end soon and we are trying to make a decision as to keep renting out or sell and buy somewhere else.

The lease with our renters is coming to an end soon and we are trying to make a decision as to keep renting out or sell and buy somewhere else.