This some suspect/millennial-ish if I've ever heard it.So in summary: We have gotten to the point where OP is scrutinizing a 39-year-long marriage, and talking about feelings, choices and obligations, after asking internet strangers about selling HALF a house (what the actual F) to someone who could walk away whenever they feel like it just cause they find someone cooler than he?

I’m trying to think of ideas to outsource several of the landlording tasks without a true property manager.  

The HGAR membership fee is a little under $600 per year, but that's a business expense and you're going to use it as a tax deduction as well as all the other expenses accrued for business related tasks. 

Increasing savings is probably the first task and a must-do.So in order of priority... 4 and then 6... i''ll be really good at saving money for the next 6 months to a year I guess.

- We’ve done our share of internet digging reviewing crime, Rentometer, etc but want the “boots on the ground” to validate our data.Any contacts would be greatly appreciated.

.#5, again include in Rental Agreement a requirement for internet access, for equipment monitoring only on your part.

I have a friend ready to pay 400/month plus the internet bill.

All the nuanced details of jobs, spending, personal cost, rehab costs can only be wildly assumed by all of the faceless contributors in the internet world. 

When the cov/decs were written, the internet did not exist.

If NONE of your deals came from anything involving internet, you pretty much are going out of your way to avoid internet.. because pretty much EVERYONE will resort to internet the second they need... well.. anything!