The short answer is: file form 1099-NEC. 

I’ll try to keep this as short as possible but I am at a cross road in life here and can’t seem to find the guidance I need. 

As the new owner, you’ll want the lease and your landlord insurance policy to take effect as soon as you take title to the property.Temporary Lease Considerations:While short-term leases can work well, leasing to a seller long-term often leads to complications.

The expectation established fell far short given all the mistakes and poor advice.

Short-short version it's hell on wheels. 

Quote from @Jake Bute: Good Afternoon,I listened to Wheelwright's podcast the other day discussing how short term rentals do not have the same rules as long-term rentals when it comes to some of the tax laws around active/passive investing.

Short version...

It is not walking distance to much but a short drive to a lot and generally a touristy area. 

But. that short of a hold period would be suspect by itself if ever audited.  

Hard money loans are another option for short-term financing, especially if you're looking at fix-and-flip opportunities.