@Ry Eikleberry, The most critical component of success in any venture (and real estate is no exception) is your ability to draw a team around you. 

Even having a couple backup plans would help tremendously & increase your ability to make the best offer for you. 

Why are you even considering doing anything but your engineering degree.

I would start with your own ability to close first.

Do you host with AirBNB because of their fees and policies or their ability to get your unit rented?

So cap rates can be higher in the Chicagoland area, but you still have an ability to find new tenants if someone moves out... this is different from other markets which sell between $50-150/SF where you have significantly lower populations, so there are limited new renters in some markets.

If that happens, and you can act within that window to lock in a low fixed rate on a discounted property, it may be one heck of an opportunity (I'm thinking that's a few months out depending whether we have a second wave of COVID, and it might very well be location-specific, proportionate to the degree of economic carnage caused by COVID).

I have confidence in my ability to do everything necessary with the exception of getting a loan. 

Unfortunately my designation and degree don't mean much when it comes to doing your own electrical, or drafting your own plans.I have a three family home, I plan to gut reno three bathrooms, and kitchens, and the building department wants stamped plans since its a 3+ unit.

At the same time, the new regulations allow for the ability to put the money back into another pre-tax account like the SDIRA.