So, it's important to note the distinction and rehab knowing that your top price will likely by the appraised price, and not what you can get someone to offer.2.

When the kids head to college, however, that is a very real and distinct possibility that we will be looking into for them - rather have room and board paid by someone else if at all possible during those years.

Chicago proper has 77 distinct communities & when you add up all the suburbs the number of communities is well over 200.  

In 2016 we saw a new trend of prices surging in the suburbs and slowing in the city center during the last half of 2016, reversing a years-long trend of urban neighborhoods leading the market with big price gains.At this point the smart investor may want to look to the suburbs...Also, the 7th ward is huge and is comprised of several distinct neighborhoods.

There are very distinct reasons for doing this that I've written many times about. 

Out of state investing = what wealthy Californians do to lose money.Do yourself a big flavor and don't mess with the equity in your own home.

Would we each apply for distinct loans and then pool that to make the purchase or would we be able to share a single mortgage between the two of us?

I combine repairs and cap expenses because there is a fine line distinction between the two on some items.  

But I also know that this is somewhat of a semantic distinction since I have other friends who continually lend out their capital to strangers who they put through their own "underwriting" process.

Although they didn't say that - I got that distinct feeling.