You should only consider switching when your current software has a significant flaw or lacks features that force you to spend excessive time on workarounds.

If you do, set a goal for how many you want to do every year and you'll force yourself to find a way to hit that goal. 

Seeing as STRs started long before VRBO (1995) and AirBNB (2008) or HomeAway (2004, now part of VRBO) this was considered when it was created.The "Augusta Rule" was a driving force.

Rents are not super high, but they will only go up.... its work force housing which I love. 

The seller already has given me a good deal on the property due to her being forced to return to NYC for work post-covid (seller is paying $20K out of pocket after overpaying for the property 2 yrs ago, and sellers agent is taking a commission cut to make the deal work).

After giving some grace, I had to turn the heat back up on them to force them to make the donation.They made the donation on a credit card, and while it's a far cry from the $50k+ in damages, it was a meaningful amount of money to them.

So until supply loosens buyers will be forced to get creative and pay up.I don’t think it’s the overall crazy demand like you’ve seen in single families driving up prices- there is just literally almost zero double inventory.I did three doubles last year and still shocked I picked them up at decent prices in Lakewood.

This will demonstrate how the property performs as a pure rental, and it forces you to save.

So are you saying it may not be wise to refinance after the forced appreciation, or does it just depend on the interest rates?

It's not going to force anything, but you can let them know "hey I'm sorry you're having a rough time, I'm willing to work with you on this but I need you to work with me as well".Check with your attorney for the deposit, in FL the deposit has to be made out to all occupants on the lease, so that could cause complications.