My goal is to have a financially qualified tenant who will be a great partner over the long-haul, which isn't going to be the case if they subconsciously blame others or the system for the things that happen in their life or view it as a favor to me to do simple things that help them achieve their goals.  

 - If you'll likely be selling this to a home-buyer and you're market is fairly balanced or buyer-favored right now, then you absolutely should fix that stuff before you put it on the market.- If you'll likely be selling to a DIY updater, or someone else who wants to add value to the property AND there is substantial value to be added (through updates throughout the home) AND your market will bear the additional price, then don't do the repairs.  

I analyzed properties everyday, from there I would narrow down certain ones to tour,  after touring I would narrow down ones to make an offer on, I would make offers that were favorable to the return I was looking for, most offers would get rejected, but some ended up working out.I believe with the 1st property, timing was on my side.  

This is, at this very moment, being discussed in Springfield: Rep Delia Ramirez has introduced new legislation in favor of rent abatement and now she has support from Chicago Representatives and Senators.

In light of this, you'll want to run your numbers strictly as a flip, even though it will be a live in flip.  18 months isn't enough time to have the buy vs rent part (or live-in part) of the investment play out in your favor. 

Abby - do yourself a favor and hire a good property manager that can communicate with tenants on your behalf. 

The crime rate seems to be high and I have not got any favorable appreciations in this area for the last 5 years.

During litigation there is more pull on potential settlements for more favorable modifications.

You will be doing them a favor and you will be doing anyone they sign a contract with down the road a favor.The way I see it with tenants and the contract is that if you don't hold up on your end, they're quick to call you out on it.

The market has been in our favor for long time so much that you could mess up a rehab but the home prices were still going up so you still made money.