I take full responsibility for my own mistakes and my own learning curve.

The Man knows wholesaling and I have learned a lot from his books.

For those that have always represented properly: there will be no issues because they will continue to follow what they should've learned when taking their classes, passing state exams, and in their "30-day orientation".The others: will fall off from confusion.Just Saying...............

Does anyone recommend books, courses, or anything to help me learn the general terms and what it takes to become a private lender/broker?

Could you text me, I would like to learn more about starting a rental Trogers

I've definitely learned a lot from them.

Where can one learn a systematic way to evaluate markets and properties for STR? 

He will be a first-time landlord and I asked him if he would allow me to help him through the process of putting a tenant in place and managing it just to learn the proper flow of how it's done and to get a strong handle on the systems that will allow us to do it.

The key is to stay persistent and keep learning.

I would suggest learning the markets and networking first.