First decide the area(s) of interest to you as an investor - both geographically and the type of investment (SFR, small / large multi, storage, etc).

Based on this recent experience, I have lost all the faith on these types of rent collections platforms.. 

To me it seems like it would be the ideal space for another unit.

My question is, if this is a deal that makes sense I do not have a lot of cash on hand - what type of lending would I be able to get or should I look for to buy and renovate this property.

It's good to meet another born and raised Chicagoan in the forums.I've found that the best thing is to stick to what you know, in terms of the areas and the types of projects you work on.

I think about the ideal customer be renting the house and who will buy it.

If you are under $2500 for taxes to me that is winning on price - just make sure they know real estate and your type of Real estate

It effects every aspect of the property and performance- the type of loans and insurance you need will change if you don't hold the property in your personal name. 

Each group tends to go after certain types of properties. 

Customers with this attitude are the type that contractors avoid like the plague .