I'm feeling a bit lost and would really appreciate any advice or guidance from experienced investors.

Aside from the obvious dangers, I’m seeking best practices and how experienced investors  in this area handle hurricane damage?

. - You'll have to learn how to be compliant with SEC requirements.Your other thread has responses from some pretty knowledgeable and experienced people.

Just wondering if there were any experienced wholesalers in my area or near me that could give me some pointers.

The only thing that would be different is that Proper covers revenue loss + all the bells and whistles  I feel I don't need for 2x the cost - squatters/bed bugs.Any input on this from more experienced STR investors or others with insurance backgrounds please?

A property management company experienced with Section 8 is crucial.

I know Sherman Associates have completed a number of affordable housing projects in Duluth (and were recently navigating another under construction in Lincoln Park that ran into some difficulties).

That is the best and fastest way in and as long as you have experienced help, you will learn by doing far faster than aligning a career to help you learn.

With this approach, I can very easily vet borrowers (no newbies unless partnering with an experienced investor for example) and focus on those that meet my criteria.   

I'm more experienced as have been in multiple RE sales (with agents and directly with owners too) over my life and been an LTR owner for 15 years and just want to do STR at this point, but if this program is legit then I would be the one searching for houses while he did the calls.