And they get their "customary" 30-40% cut of the winnings!

If you rent out property and want to sell, you need to just cut bait and sell, and it's obnoxious not to let your tenants know you are going to be selling. 

In the mountains I imagine it is a hot tub, views etc.Using a tool like AirDNa can cut down on research time sifting through listings and gives you a better idea of occupancy. 

  $200/ MO CF is our cut off on any deal. 

If we go by the BRRRR method, we're already going to buy and rehab it, then would it not make sense to just flip it at that point and cut out the need to deal with tenants, home damage/repairs, refinancing, etc.?

We have family ties to the Tampa/St.

This is a big problem as its cutting off my rental income for all the blocked time on VRBO so any insight is greatly appreciated.

Of course, have a plan to pay it back but it's a great way to utilize money that is basically tied up, and losing value since in a couple years it won't be worth what it is today.  

The easier way is to have a penalty of 1 month's rent and then it is clear cut. 

His hands were tied and he ended up having to use cash outside of his IRA, which I believe would have been flagged as a prohibited transaction, but he couldn't just stand idly by while his tenants had no running water, etc.