It can get pretty expensive to invest this way. 

I've read a lot of bad information on how some gurus are promoting techniques that are flawed at best, fraud at worst.

If you want to check out a pretty cool interactive map that shows tax data for every state, and even county, check this out from SparkRentalhttps://sparkrental.com/states-with-the-lowest-property-taxe...

Accountants is a pretty broad title.

Reason I ask is in note investing it is actually usually pretty difficult to lose money consistently, thus the questions. 

So, if you don't know how to build financial models, there are some available that are pretty good online (adventures in CRE is a great resource).  

Even when talking with some real estate professionals who would seem to have an incentive to help me with renting out my property, I have been met with serious warnings (they pretty much say don't do it).

Aside from this forum and the events promoted here, where else would you recommend looking to find connections or events with experienced flippers in Chicago? 

(your 55 days of vacancy was for the most part the holiday period).Vacancies are pretty high and based on BLS statistics, population growth has been flat. 

@Owen Rosen the links you shared pretty much only state a tenant shouldn't have to supply liability coverage to their landlord.Of course they will say this as the provider does NOT want the extra liability of covering additional parties!