It's been one week of me doing this so far.My question is: is this OK to do in the short and long term?  

I have my listing on Airbnb but I would like to list it on many more and manage them (Expedia, booking, VRBO, etc.) with a single mailbox. Any suggestion on what service to use?

Is there potential to use it for AirBnB or some other short term arrangement to increase the income?

I have not purchased anything yet, but I have discovered a few opportunities. 

This would get me the property essentially free BUT would leave me with almost no passive income (break-even) because the rent is not high enough, the mortgage would be for 134K, the property tax is not helping and I would have to close twice in a short period.What am I concerned about:1.

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. 

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.  

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