I'm looking hard at Aurora and some pockets of Rockford, and I'd love to learn more about some areas of Cook County. 

This is exactly the kind of cockamamie scheme I'd cook up to break this lease at minimum cost.

How many meals a day are home cooked vs. eaten out or pre-made from the store?

What gets tricky is that if that original pot of money included parameters like it is interest only for 12 months - and then you end up doing a loan for longer than 12 months - your monthly payment on that loan may be higher than what you are getting in payments from your borrower.

The goal should be to have insurance and as much as you can get (even an umbrella policy), AND establish an LLC that works with a Asset Management Liability Company, that then works with a Domestic Trust and eventually when you have enough in assets to warrant it (500k-1.5M in assets) a Foreign Cook Trust that can be used if an event tiggers the foreign trust.

Not saying this to be discouraging, just saying the midwest may not be the pot of gold at the end of the rainbow that some may lead you to believe. 

Here are the details:purchase price: $85k + $3k closing costs = $88k acquisitionrehab: $25kARV: $150kannual taxes: $6k (it's Cook county)After it's rehabbed, he says it will likely rent to a section 8 tenant for $1687/month.

They love to cook?

Why don't you just pick up the phone and ask them what their intentions are behind paying the full year upfront, this way they don't have time to cook up a story about it and you don't have to wonder about the what ifs.If they have two years legitimate tax returns and the income is verifiable than I personally don't see a big deal.

Remind him America was founded on immigrants and prides it’s self for our melting pot of diversity.