I pushed the sellers to contact the City to square up and wound up having to negotiate directly with the City on what repairs would be required for them to issue me a COO after the sale.

Some residents can argue that it isn't fair as it isn't billed on their actual consumption but rather on the units square footage and/or the occupancy at a point in time. 

I mentioned it to family and they "red lighted" me.

In the process of finishing the basement to increase our square footage.

This deal is intended to be a cosmetic fix & flip with 4beds, 2.5baths, 1,916 of square footage with a 2 car garage.

I would consider that a red flag and cause for concern in the future.This opinion is based on the fact that I would personally pay full price for my significant others products or services offered in a given venture.

It was good when the market was red hot, now you're going to need a sales person (realtor) to get the property in front of as many eyes as possible 

Vinyl and one dollar square foot carpet will be your best friend!

This is a big red flag and unless you have a straight forward way to dramatically decrease this expense ratio (and convince investors on your direction to decrease this), I would stay away. 

On the other hand, the judge is a homeowner and he's going to know, yes, probably off the top of his head, that if you really wanted to do the absolute cheapest possible vinyl floor fix it would be DIY peel-and-stick 12-inch vinyl tile at Walmart at about $12 per 10 square feet.