Post on craigslist, post on marketplace,  get A LOT of lines in the water and you'll be more likely to catch a fish.

We don’t feel great about it for various reasons, namely it’s a liability, an eye sore, and we don’t know of all the problems this could present.Has anyone had this happen?

Just wait until you or someone you love becomes disabled and you'll find yourself viewing those funky features with new eyes.

If the numbers work, I think it makes sense to do it while you are still there, learn, build systems, have a handyman, and then have your parents be your eyes and ears, not a PM.

Definitely incorporating that into my STR.

Bringing your family along also puts a serious damper on that the primary purpose of the trip was actually for business - not impossible, but in my eyes it definitely taints it in a way that you really want to ensure everything is buttoned down on the business purpose and the actual business activity that occurred.

It is more about having a eye catching unique landing page, which is the same function that the categories/unique stays provided. 

Things to keep an eye out for?

One day, my wife came home from a tough meeting with her manager, tears in her eyes, and said she couldn't take it anymore - she hated her job and didn't want to work anymore.

If ever you need a second set of eyes on an investment let me know, it would be my honor to help a US Marine.