Most of the repetitive things I have automated including: cleaning, restocking supplies, laundry, guest messages, dynamic pricing, etc. 

Make bunny suits, respirators, gloves, goggles part of the process and make sure there is running water for cleaning on site.

Im a nice guy so after 30 years of him living there I would pay a couple hundred bucks out of pocket to a cleaning company for some deep cleaning (to show my appreciation).

To keep it all simple and clean I just want to pay him a set interest amount on the money he puts in the deal.  

Anyone can find a contractor and then have to deal with cleaning up the mess afterward.

It's completely clean.

Paid $1,000 for someone to come clean and haul everything off.

With that said, I'm not trying to be just comfy forever and that's why the last 6 months I've been really digging deep into learning about REI so I can make it a side hustle that one day I can maybe quit my job off eventually. 

Sure enough, soon after they put a notice in everyone's mailbox, my relative saw some steps taken by some of the neighbors to clean up their lawn and spruce up their homes.

Be prepared to "waste" a lot of paper towels doing this, an irresponsible amount. 100% silicone caulk is extremely sticky and slimy, and you have to keep your finger clean as you work.