In response to the suggestion of partnering to pool the 20%, I do have the funds to meet him halfway and get to that 20% mark but wouldn't the issue arise that down payment money cannot be "gifted"? 

It is located in the Willo Historic District, which is a very popular area and has always had higher property values.

Does anyone have experience with this issue arising while in escrow?

Small, cheap houses or mobile homes that are in close proximity to the base are popular.

This alleviated some of the burden of finding tenant replacements and also helped them out.But to @Damaso Bautista's point, if it's a competitive student market, and there's already a concern before you sign an agreement with them, I'd seek other tenants so you don't have to worry about that situation arising.

I might just be missing something, but I'd love to hear everyone's opinion on HomeReady vs FHA loans and any reasons it seems to be less popular.

I'm around the Chicago area as well if you ever want to know more about the market here, or more specifically about property management arrangements should the need arise.

I do not expect a rise in foreclosures as demand for properties remains strong and people are still willing to pay high prices for distressed properties. 

I disagree with your assessment about being negative and I believe my question regarding what is or will be different about your software is a very popular and logical question. 

I recall them being quite popular.