My tenant doesn't want to leave, but I have transitioned her to a month-to-month lease. 

I assume if you're using him and liked him when you worked on buy side it would be the same (unless he just doesn't think he's making enough money off it and it's not worth any work).

Just because someone has screwed you over in the past, doesn't mean that you shouldn't trust the next guy. 

Rent doesn't appear to cover expenses.

With that said, while moving out might have been the best thing you could have done for your own emotional health, that doesn't mean your LL has to "eat" your moving out with little or no notice. 

I would say you are doing a BRRRR, the fact the previous one is long-term doesn't matter.

The landlord won't return her calls for months now (she major septic issues and had to pay out of pocket, amongst other things), has blocked her daughter on fb & she doesn't know what to do.

Most contractors are reluctant to walk a property with someone who doesn't own the property.

To basically discuss with them that this doesn't appear to be the right situation for them. 

As long as it is a cash flowing property that doesn't have too many problems(plumbing issues, a major foundation issue(all houses settle over time, but some house are built on very poor soil), and as long as you don't have issues finding new renters(takes months and months).