Short-term rentals aren't passive.

(An exception is if you own 5% of the company you work for)Agree, this is a great summary post on REPS with core concepts on how to qualify. .I think the complexity comes in when people have edge cases - it becomes difficult to write a simple short post that educates everyone.

I own a property in the Disney market and co-host/manage another 25 in the area.Disney I think is a good market if your goals are more aligned with traditional long term real estate goals, and a bad market if your goals are more immediate gratification and short term cash flow.The major benefit of the Disney market is that it's about the safest market you can find from a long-term perspective. 

Stick to short term goals. 

Our first investment will be turning our primary resident into a short term rental. 

I think this is the gift and the curse of a still emerging asset class (short term rentals) - as it becomes more "institutional" i.e. more like commercial real estate with more sophisticated buyers then financials and systems for this will likely become more streamlined and stable, but we are still in a place where the buyer pools are more newish investors or typically residential basic investors, so not has experienced or sophisticated evaluating investments based on a detailed financial analysis like more seasoned commercial investors likely would.anyways, just a guess on what might be going on here

If there are 8 months left, not much you can do in the short term.An investor can buy the deal, and wait until the lease expires, and send a non renew.You can always offer one of the residents an incentive to leave, such as cash so you can have a vacant unitGino

This is assuming you are talking about a short term rental and not sub-leasing as a LTR.

I don't want to fork over 50 K into a tree that will rot in a relatively short period of time.  

Deciding to BRRR (Buy, Rehab, Rent, Refinance, Repeat) instead of selling makes sense if the cash flow and ROI are better with the property as a short-term rental (STR).