It's in a more remote part of WI directly on the lake and I'm attempting to save on cleaning costs/time/maintenance costs by going this route as well as make it more marketable to smaller groups. 

If the home is in foreclosure with a sale date that will pop back up after the moratorium is lifted it may be risky to attempt a short on the 1st.

I am kicking around the idea of setting up systems in attempt to acquire off-market properties in Illinois.

David is giving himself far more work and will have far more vacancy because he's attempting to play matchmaker.

I would suggest attempting to get at minimum a 3 yr, lease signed.

Hail mary attempt but maybe there is a creative solution?

Are you attempting to whole-sale?

I believe that attempting to invest with the same monetary plan as one would purchase a primary residence is not investing at all. 

Heck even their sales tax will rise again in attempts to address their financial crisis. 

There are people who have attempted this as well.https://medium.com/geoai/house-hunting-the-data-scientist-way-b32d93f5a42f