I'm thinking $1.99 / month / property feel like the breaking point for me, where more than that and it would save me money just to flat fee the utilities and accept paying out of pocket for an occasional tenant overage. 

I occasionally come across some REO properties that had high tax appraised value in the previous years.

Mostly buy and hold but I do like occasional flips.

You will see that occasionally because the broker is trying to get top dollar for the seller and create a mysterious bidding war.  

Most of the time they are wrong and occasionally they are right.

Also, when looking at places around the US consider places you might like to visit for a tax deductible trip occasionally.

I didn't have a job and just did occasional consulting and traveled the world for fun.

Accept the fact that all rental property will need maintenance and occasional repairs.

Frequent, extravagant, or lavish trips might attract more scrutiny.

I have my primary home that I Airbnb occasionally (both a private room and the entire home) and I just bought a full-time out-of-state SFH to be a full-time rental.