I personally never listened to him.. what was it that you liked about him ? 

Only the person running the club chooses potential investments.

But since that is the choice you have made: I don't know what it is like in Pueblo; but in Mesa County where I live there is a person on staff that walks you through the process and the necessary paperwork that needs to be filed (they don't fill it out for you - just provide the steps).

I've been hearing about problems in the insurance industry but this is my first time experiencing it personally.

Whether that be starting the side hustle of real estate investing, or finding a new job, but, personally, I would not suggest you leave a well paying job until you have started down the path of real estate investing on the side.

What is your personal situation?  

I've seen some posts both here on BP, in local FB groups, and heard comments in person corroborate this.

Flat fee services, multiple layer and level packages (Silver, Gold, Platinum) have accompanied all kinds of other offerings, tenant and eviction insurance, marketing fees, reporting fees, tech fees, and even talk-to-a-real person fees.

What's the reason to repurchase - for personal use or investment?

He has personally helped me with insurance in Michigan and has worked magic for me!