They don't communicate well, don't take responsibility for their actions, do not clean or maintain homes well, and will shaft you when it's time to leave.Other than that, it's a pretty good system.

However I am struggling to understand and evaluate the risks involved with cash out refinancing 2-5 years down the line.

If the unit is empty, change the locks, clean it, and get it rented.

Are you not charging the guests a cleaning fee?

Prior to clean up make an inventory even if burned.  

(Just need to clean filter every month? 

When they move out, I can access their account to charge for cleaning and repairs.

In the case of GEG, we let our members know we did not have a track record with them - they were new to us and just being tested - and therefore it was even more important to perform thorough due diligence since we can't be involved in the transaction. 

Now what you should do is contact the title company and confirm if title was going to be clean and marketable.

He does not want to deal with the headache of tenants cleaning or any thing to do with STR.