Property management is really important, though, so I would start getting educated on the intricacies prior to trying it out.

On top of that they will be paying you to teach you the secrets of intricacies of their business (like college but they pay you)

With that being said, do you all recommend a newbie like myself first learn the intricacies and math behind successfully flipping properties before learning the intricacies of wholesaling including marketing?

I'm not sure how that would work when you are dealing with multiple parties (because the trust idea works on the premise of an estate planing and don't know how you can make the case for that with unrelated parties), and that's why you need specialized advice from an asset protection lawyer familiar with the intricacies of your situation - contact @Scott Smith and he will be able to give you proper consult.Insurance and asset protection is not one and the same, nor a question of one vs the other.

Traditionally I have always done my own taxes, but now that our portfolio has more than doubled (also looking at a duplex in the Spring), I am in need of someone who really knows the intricacies of real estate tax laws to maximize our return for years to come.

Traditionally I have always done my own taxes, but now that our portfolio has more than doubled (also looking at a duplex in the Spring), I am in need of someone who really knows the intricacies of real estate tax laws to maximize our return for years to come.

It seems like we're best cultivating a relationship with a local insurance broker in Chicago so he can field out the intricacies. 

If this were a forum for maximizing profit in sales tactics where we can discuss the intricacies of getting paid for a diagnostic service call regardless of whether you actually diagnose anything correctly, well then...

Where can I educate myself about the intricacies of buying from the Sheriff sale?

You should decide to either learn the intricacies involved in this yourself and/or commit to finding the best professionals to help you with it.