The building is highly inefficient so we are mainly looking to replace the electric base board heaters, replace windows, redo some drywall and insulate where needed.

The main focus is the property not the person. 

My main concern is it will appraise for less because it has piers.

QUESTION: What other factors and numbers do we need to crunch or consider to figure out the best option?

It's behooves the individual to really understand that there are a lot of conditional factors and risk weighting to be done, per individual goals, and per deal. 

Doing a little research, I'm starting to uncover some of the local laws (mainly from https://www.courier-journal.com/story/news/politic...)Right now I'm tracking a $25 registration w/ revenue commission and obtaining a conditional use permit.

I'll have the plumber (or handyman) coordinate with the tenant to come over for a more emergent situation like a main line clog or no hot water. 

It's down the road from our high school, an elementary school, and the main drag.

That being said, many of the courses from the MA in RE degree you outlined are offered online and in person in NY.

In fact it may even create some more tax return complexity but should not increase nor decrease your tax.LLC are mainly used for liability and asset protection.