I do like the fact that he is young because I think he is wanting to build a reputation.

I'm an nco E-4 and have a good reputation (MoQ, Meritorious corporal, cert comms).

-After 6 months building some reputation, the property should gross $200k per year in vacation rents, or ~$16k per month.  

Having a mentor is great and I wish I could get one in my area but I couldn't find one that was willing so I dove in by building a team. 2 RE agents 2 contractors who I researched to make sure they're reputable and several other investors.

Suggest you contact your local home builders association, reputable contractors are members and you can get a list.

Not to mention the reputation the shareholders will get when "they screwed their staff".

I work with Cliff Ashburner, who has one of the best reputations in the city for "dirt law."

As long as they are legit and reputable it dosn't matter where you find one.

I've had some great feedback from weddings in the 100-200 person size, I need to find the right person to put in charge of that initiative, but with a bit of seasoning and reputation, I can likely do 15+ of those a year at $8-12k+ per weekend.

Part of your strategy then needs to be in making it clear that your client can close, and you need to foster a reputation in the market that you are an agent who gets the deal to closing.