Already W-2 Employed and only doing it for the education aspect (apprenticeship program) barely netting 20k a year so funding a househack is not an option my current path.

Went to Bare Bones gastropub - good beer, good food.

GEt her out, don't do the 2000 renovation, just do the bare minimum to get it rented and get a better tenant in.

However, I currently barely clear my bills and my credit is shot from when my wife lost her job last year.

Bare in mind 24 months from now plus the spotty pay here probably puts that rate north of where it is now and that is baring any market movement of the rates in general.  

You did not agree to this monstrosity of a security system and to the ridiculous prices it comes with,it is not your problem.There are newer wireless systems that cost like $200 to self set up and barely 50 bucks a month to monitor that they could have paid for themselves.Don't make their problems,yours!!!

The investor I sold it to didn't care one bit because he turned around and sold it for almost 40k with barely any work.

I barely touched the 2nd property and don't plan to touch houses moving forward.  

You can barely tell the really pricey stuffJust get a good quality product, I would pay at least $4 SF for the material.

I don't have experience with STR, barely in process of purchasing our first one,  but I do have experience with my other business.