I replied, "I just bought the one caddy corner to you for $95k, it is a four bedroom, yours has three what is fair to you knowing you won't have to pay any Realtor fees, clean anything, fix anything?"

If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

I have contacts who routinely install hot tubs at every STR property and do well; you are in a market where there will be professionals who can help maintain and service a hot tub. 

Challenges I face include accountability for my team and having a consistent, affordable cleaning team.

I have a Villa in Tulum, Mexico and am having a hard time understanding how much of the "Host Payout" actually goes to me, because I would think that the entire $665.57 would be mine but it looks like they deducted the "Cleaning Fee" and "Remitted occupancy tax" the "cleaning fee" I understand but am confused on where the "Remitted occupancy tax" is going.

They are cleaning/maintenance specific tools.

I mainly did clean up and prep for the contractors to save a little time and money, as well as some painting and sealing.

People want it to be, it's very cool and hip, but really the masses just want nice clean, functional and affordable housing.

Id think the toughest aspect is making sure folks mesh well and either a cleaner is paid or there are set instructions for cleaning on common areas. 

It sounds like it would be easier (time being the best asset) to just sell and pay taxes up front if my goal is to get a clean break from Cali?