Dealers/movers definitely know what they can get, and private sellers follow suit so you'd have to be motivated/connected AND be able to move fast to find a fair deal on a decent 'newer' used manufactured in the first place.I'd probably go new 75% of the time vs what I've been able to find price wise, used, personally..

This is completely up to you, If an individual came around with perfect credit and met your other income requirements I assume you would rent to that person.

HOWEVER, I do personally make over $100k/yr cash flow from 16 properties here.

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

Only the person running the club chooses potential investments.

but it takes time and effort - like going to the market IN PERSON, and setting up a team IN PERSON. 

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 understand that working with professionals decreases the likeliehood of this happening (and this person is a corporate America professional) but thought I'd get some insight from this very well versed community!

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.