Most gulf front investments are mostly appreciation plays unless you do a serious renovation.

The STR, if purely an appreciation play,  is speculation to me. 

However, if you ever want to replace that home, you'll have to move it off his lot.I would consider appraising the vacant land and trying to cut a deal that's fair.

Playing the long game, it's not for those chasing rainbows, definently for the LT planned methodical focus. 

If you're aiming for growth and can secure a low-interest mortgage, financing might be the better play.

To be fair, I've never actually met anyone who says they've had a note called for this, but it is clearly in the loan docs and is the right of the lender to do so, should they choose.Cheers!

I have a contrary play. 

If the issue is no direct fault of the tenant then I do not think it is fair to charge the tenant anything.

Perform the same task in each app to ensure a fair comparison.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.Run a credit/screening report on yourself.Enter a maintenance request, assign a vendor, and attach a fake invoice.Enter charges to the tenant's ledger.Enter recurring charges and automatic late fees.Sign documents electronically.Run owner reports.After testing a few apps, one should clearly stand out.

The FHA househack strategy is fairly common and pretty straight forward, a lot of people have been using this and/or the conventional househack (myself included) so have been on both sides of the table.