You can establish the land trust and remove your name from the public filing as owner, allowing for some anonymity.

Can I get her to sign an agreement giving up all rights to property effective 1/12/19 that would hold up in court? 

It will put another barrier to removal (takes a few days up to a week for ACH transfers between institutions).

Based on your figures, you are around 80-85% now so PMI could be removed or nominal at best. 

HVAC tech thinks the simplest path is to remove the oldest big furnace and replace it with a new small furnace for one upstairs unit, install a second new small furnace for another upstairs unit, then use the newer big furnace to heat the main floor. 

I feel like this would greatly effect who comes in the door but these properties are very affordable ranging from 105000-160000 and if it’s good to invest here I could potentially buy multi down the road.

My take is that emotion needs to be removed in the business side, keep to facts, laws, rights and be clear.

Sidewalks are a huge one especially...the city/town/village owns the sidewalk if you need to block it for some reason (you need a permit), but come time to replace it, remove snow, etc. it belongs to the property owner.

Purchase a home that needs small updates that could be an easy flip in value and stay there while you renovate, then refinance or remove private mortgage insurance, followed by renting it out.

But what long term effect does this have for banks and then those that have to report earnings with more and more dead beat properties on their books?