This helps me track net worth.

It's illegal to run a credit check on someone that you're going to turn over an asset worth hundreds of thousands of dollars to?

Remember you have to pay income taxes on your profit, figure 20% for that....

If I remember correctly the non-profit would initiate a master lease with you and then work to sublet/place the individuals there. 

You can most certainly get a loan on an investment property....consider connecting with @Landon Hoon or @Michael Barbari both local Chicago lenders.If you are looking for maybe something a bit more aggressive on the down payment with hard money let me know and I can provide some other contacts.Partnering will be the best way with no money...it's not easy and you'll have to be willing to do all the work...but worth it in my opinion.

Not wanting to look into smaller towns or communities up north I assume it'll be a tough battle to find something worth while that doesn't need too much work.

It also drastically brings down the Net Worth ROI when you put 20% down vs 5%. 

I invest in Jacksonville FL where the homes are worth in the low 200s.I find that CPAs will tell you to have one LLC for each property... maybe because they can charge you more per tax return :)

Wondering if its worth it, as I know the development process and have good civil, architect and GC contacts.   

Remember; pigs get fat and hog's get slaughtered.