You have to have skin in the game.   

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.

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

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

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

Give up a bit of projected return for an established operator.  

Ask discovery questions, genuinely care about the answers, and seek to find a solution that falls in line with what is important to the owner.Aim to first establish trust with the owner.

When you get into development, particularly larger developments like major apartment complexes and/or subdivisions, the game is heavily focused on political connections.  

Thus it becomes a "location" question, is yours visible and accessible.These National companies are playing the Average of numbers game. 

This property is going to be a money pit for a while, but long game will most likely show a profit or at least not a loss.