Could this be an easy fix with a new roof and carpeting, or should I reconsider???

If anyone wants to play devils advocate and warn me why I should reconsider a deal like this please let me hear it!

(and trust me they will pretend to LOVE the place and throw stories or feelings at you)Don’t be that guy and if seven walk through and you only get one to fill an applicationyou might want to reconsider your pre-screening process. my pre screening process saves me time from showing people the house who won’t like it and aren’t at all qualifiedBefore you even agree to show them the property, ask the right questions!

But if the definition can be a bit more dynamic regarding all the variables that comprise an investment, maybe those people should reconsider the investment rather than walking away. 

Good luck with your project and reconsider your position of not using Realtors.

I don't want to sell, but I'm starting to reconsider holding them if I'll never be able to access the equity. 

You may be able to justify this if it is an all-cash purchase and you self managing the property and even that might be somewhat questionable, so you really might want to reconsider this deal before moving forward with it. 

After that I outlawed dogs and cats.Now I'm starting to think I should reconsider and accept small dogs under 20 lbs.

You should probably reconsider having him serve in that capacity based on his clear lack of good judgment, or at the very least make him read the landlord-tenant handbook front to back, especially the part about a tenant's right to privacy and the part that states: "any uninvited sexual advance, solicitation, request, or demand for sexual compliance is considered harassment" (at least that's what it says in the handbook for my county and I'm sure something similar appears in most if not all).

And fair point on the tenants being responsible for snow removal, I'll be reconsidering that on future analyses.