2021 hit and that is when I became financially free and was able to retire from teaching at 55 yrs old.

This will teach me alot.

The challenges in real estate teach you invaluable lessons that you might not gain otherwise.I also invest in Chicago, so I have a few thoughts in response to the questions you raised.

You'll be hard pressed to find a coach that teaches Lacrosse, rugby, cricket, and shot put.Also, a coach is typically used to accelerate growth, not get you started.

Are they teaching on what you want to learn?

I'm joining Bigger Pockets to try to connect with people who can teach me and encourage me.

Everything he teaches about personal finances (budgeting, car loans, credit cards, etc.) is spot on.

For management, self-managing saves costs and teaches valuable skills, but a property manager is essential for out-of-state properties or scaling your portfolio.

There's no $$$$ in teaching you how to implement the action items I shared above which is why the higher revenue generating systems are sold, usually to real estate investors who don't know any better. 

A better solution, in my opinion, is not to rely on wholesalers,  as not only is it a dying breed due to the sheer incompetence they exhibit due to gurus' wrong instructions and teachings, but, wouldn't it be better to generate your own leads through a high performing website?