Learning something new everyday!

My first idea is to buy a STR, something small but in a area where there is a good demand for STR.

This is something I want to do as well 

I recommend you never sell a property unless you have a firm plan to invest the money in something that produces a better return or moves you closer to your goals.

If so, you may have a chance at getting something back, but as @Nathan Gesner said, it will rarely be worth the money.

I want to run something by you all and get your thoughts.

On the other hand, you and I both know that this will lead to a TON of calls/complaints/negative posts on social media about a disagreement of whether a previous building professional should fix something for the new owner once out of warranty, not the contractor’s fault to begin with, etc.

Appreciation is great, but I'm not going to buy something and be out of pocket for years & years. 

Were you able to figure something out?

They currently pay $1350/mo for the rental.Are there any creative options for making this work or something we're missing?