FYI - It is not setup for rent by room. 

We had too much rain in the spring, so we weren’t able to set up the property in order to catch the height of house-buying.

We are primarily looking for land on which to set up an owner-occupied situation with 1-4 rentals.

Switching property managers seems like it was a smart move, especially with how much you and your wife had to step in before.Chicago definitely isn’t an easy market, but it sounds like you’re set up for better success moving forward.

Long story short: 5 unit multifamily set up with frontier internet.

This house had 12” of water/ice in the basement... there’s a nice sump pump set up just sitting there with no power...

If its little down or nothing down then of course this is a hard no.. this could be set up pretty easy to rip rents.

We are now at the stage of working with our international accountants and lawyers in order to set up our entities correctly.

It's free and you'll see what problems other people are facing and how they solve them, which will help you decide whether or not to move forward with your plan.It's possible to find a reliable person who would be super happy to have your rural set-up and not have to have a down payment to buy it. 

It takes actual thought and a programmer's mind to be able to build a CRM into something that's actually effective (sure a basic person could setup a phased text message or email automation, but it's tying everything together with opportunities, automated campaign re-entry/follow-up, social media integrations/automations, etc that is the real value).