It’s difficult to bring in a contractor to bid something you don’t even own during the due diligence phase.  

@Vernon Calhoun and @Whitney Hutten, if you ever need any answers or boots on the ground in Little Rock, feel free to contact me.  

I understand when your in the learning phase you just want to make sure you are analyzing properly.  

Income in between $100k-150k causes the maximum deductible loss limit to phase out.

.- Garage/Backyard: Yard is standard Chicago size with above ground pool that takes up most space (girlfriend wants to keep, I want to get rid of haha).

Putting in more money isn't even close to being the answer and you don't have the intellectual honesty to ask "what is the answer" from someone who knows the ground level.

it currently sits on blocks and is about a ft and a half off the ground currently.

I think the biggest mistake you can make is NOT doing either and never getting off the ground. 

That's the best way to gain experience, and then when you're ready you can hit the ground running. 

If you added a pet addendum, then it sounds like the pet is no longer an issue, or grounds for any legal action.That leaves you with the unauthorized occupant, However, if you have been accepting rent payments despite knowing about the unauthorized occupant, you've essentially given them permission based on the legal principle of waiver.