Welcome to BP community @Justin Paradis  It is a great place to meet new friends and learn about various aspects of real estate and more.

I don't have an issue with this aspect of the analysis.

Then for rentals, you would want some durability to go with affordability, so look up,  via the search function, the threads on how to harden a rental for ideas in that aspect. 

An online LLC is usually not worth anything, unless you follow all of the required formalities.One aspect of a separate entity that can provide a different kind of asset protection is possible tax liability.

Constructive criticism and positive encouragement are welcome!

My partner will, because it sort of is.I don't mind people being critical- It provides things to consider.

You have come to the right place to learn about all aspects of real estate.

You are right, contractors are likely the biggest obstacle to a rehabbers' success, so this is a critical piece to get right.  

The less tangible aspect of the cosmetic changes, but in my view, most important, is how it will likely affect the change in tenancy.

I say could because you still need to research the other aspects of the neighborhood and future potential.