If you feel the need to let them know you will be taking care of any outstanding maintenance requests, that may be positive news for themGino

You’ll also pay transaction fees disposing the asset, likely in the $40k+ range.I don’t think you have a clear-cut answer here, but you’ll need to rack up all the financial trade-offs to make an informed decision.

I find most times if people take care of their car, they'll take care of their home. 

Think carefully before you do this. 

The heavy cleaning and repair costs after longer stays are definitely pain points but I've seen my clients make it work by screening the tenants more carefully for MTRs, doing bi-monthly checks to catch issues early, and writing clear lease terms about maintaining the property.

Would rather have these renters than my buddy’s who used a chainsaw to cut the sink out when they left.  

With short term rentals, you tend to take a larger cut as there are many things involved in the day to day upkeep, think 12-25%.

Also, I think, general maintenance is centralized so 1 handyman could care for all units, which makes it easier to manage.

Although not a big deal, my tenant that is renting my property through THD is typically more demanding with an attitude of "I don't care, the insurance company pays for everything".

Not sure if Im over thinking it and people dont care or maybe one I day get a bad hit.