About four years ago, I transitioned all my long-term rentals to short-term and vacation rentals, and it has proven to be the best investment decision I've made.

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. 

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

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

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

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.

So condo's can be a good deal if they are in an area that has a lot of vacation rentals and the municipality is all about tourism and space for visitors to stay.The biggest issue is the HOA.

Give them 14 days to vacate with no penalty.