I got paper work signed and she vacated!

Decent rentals are hard to come by, since we live in a "vacation town" a lot of the previous rentals have now turned into Airbnbs.

Adam, I am vaguely interested in BRRRR to vacation rental in cottage country to play the long term appreciation game.

I’m looking at a $20k make ready after long term tenants vacated.

in addition to everything else, it would bother me to pay a bad tenant to vacate.  

As well, im starting to see vacation commercials for Springfield, IL.

If you want to take a vacation, be out sick for an extended period, or even just move on, you'll need to "hire" and train a replacement.In terms of "The Cashflow Quadrant" (E - S - B - I), you're in the bottom-left corner: you're self-employed.You would need to move to the top-right corner and become a business owner: the business needs to run even when you're out sick, on vacation, "on family leave", etc.If you're new to the concept, "The Cashflow Quadrant" looks like this:E | B-----S | I"E" is you're an employee in someone else's business. 

The idea of moving to a vacation property and wondering about cash flow to replace your OR rental.2.

Your home, has to be in good condition & you will have to ensure that the tenant can vacate the home. 

I like your plan of investing in vacation homes.