This is very similar to my schedule (some of the bulleted content you have may vary or be included with other messages) but since I've also starting using Airbnb recently as a guest ( a lot ) it is interesting to see what hosts do and this does feel like a lot (hence the contradiction).  

Not sure what state you intend to get licensed in to start, but before you get too far along I would check with the Real Estate Commission to confirm that your end-game (AI decisions only, no human broker in the loop) will pass their muster.

Maintenance and cap-x does not, in large part, have to be a mystery game of wait n see what happens.

Thatch Nguyen (for those familiar with him) really popularized this on the west coast in Seattle.Is anyone planning on getting into this game?

this can vary from 25%-75%.   

I use it daily and find the results vary by property from very accurate to wildly inaccurate. 

It would be good to understand what other think is a good net operating profit, cap rate, and ROI in today's world which I'm sure can vary by market. 

But with all things your mileage may vary.  

Yes, demand is there, but price points vary. 

I would say to find a better property manager, but it sounds like you're leaning towards getting out of the game.