I learned this after I did some more research. 5k on 100k LOC is really good when you compare it to a hard money loan, however, the damage it will do to your credit score short term is too much of a risk for me. 

Over the past 5 years, we've renewed, updated, and remodeled the building to attract better quality tenants (we have 5 residential units upstairs and another commercial unit).

I worry about city/government restrictions on short term rentals, but am not familiar with current laws in Chicago.

It might not make sense to do a 1031 exchange.In PA, state income tax will be due on the gain even if you do a 1031 exchange.You will have to pay a qualified intermediary (QI) to handle the 1031 exchange; that might run in the ballpark of $1000 or so.If you already held for a year, you are now into long term capital gains tax rate rather than short term.

I'm doing the best I can to manage the volume, but I fall short sometimes.4.  

I Am attracted to low crime areas, better schools, and newer construction if you are looking for a low involvement investment, especially for a first property.

The ability to leverage your 100k over multiple projects makes it more attractive for additional RE income and also long-term appreciation.

BRRRR properties are normally purchased with short term financing (Hard Money, Private, Money, Cash, and a few other methods).  

I've worked for a company that put in about 50 mid range boilers over the course of a few short years and spent about 50% of my time just trying to get them to limp along in the winter.

No one abuses them/has friends over to do laundry like a free w/d would attract.