@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. 

Rustic industrial (or industrial chic) also seem overdone, but I do think we will continue to see certain elements, such as metals and light fixtures, continued to be used from this trend. 

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?

The bulkhead offers more defense against critters and the elements. 

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.

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

Not just "I can do it" but "its' what I do" there's a huge difference between the two and the former using does not end well.Al that being said the single most important element is to know the market intimately.

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