I am sharing my experience as I believe that TIME is the ultimate currency in life. 

I would be leery of an product or service being promoted that has zero negative reviews.A 1-star review is often not realistic and will tank the algorithm in your first year for sure because it's not balanced out yet.

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? 

I think overall life satisfaction is very important so ultimately have to do what’s best for you.

I envision this portfolio supporting me during my retirement years—though I still plan to work, just in a different capacity than I do today.I recently finished reading "How to Invest in Real Estate: The Ultimate Beginner's Guide" by Josh Dorkin and Brandon Turner, which has been incredibly helpful.

Unfortunately the people who promote them do a great job of selling the dream of high returns for zero effort.

My ultimate goal is to learn what investors are looking for from me as a wholesaler?

He has a team to whom he delegates some of the coaching, but ultimately Brad himself is looking at your deals and providing feedback. 

Start with BiggerPockets Ultimate Beginners Guide (free).

@James Carlson You probably already know my thoughts on STRs vis a vis 'affordable housing' :-)But this is going to play out as it will, and ultimately even Gov't intervention/restriction will fall to the power of the free market, so we'll see how it goes.I wish the property owners and entrepreneurs well, although some of them will learn that 'elections have consequences' as 44 so famously said.