Recently moved to the poconos and a lot of wealthy people move to the area from NYC and neighboring states, seems like finding buyers will not be hard if the deal is rightlove to get the conversation started and please correct me if I’m wrong on any point.

It's not just the content, but the culture that he's built.

Part of the reason to build wealth is to not sweat 1-4 weeks of lost rent.

If the real estate market crashes you lose your job and your wealth. I

Wealthy 2nd homeowners looking for someone to manage their home 11 months out of the year will gladly pay higher fees if you can demonstrate you’ll properly take care of their home and perform well.

Generally, your idea is a good idea since you’re really leveraging your housing allowance to build equity and wealth. I

Difference in weather, culture, etc. might be too much year around for you to enjoy.

Pop culture has made it acceptable to vilify property owners/landlords because they are the "nemesis you see" when you cannot pay your rent. 

People have grown wealthy starting out just how you have described.  

We're trying to raise a portion of the funds for a small resort (6 cabins) from private individuals and I'm running into some difficulties: The whole real estate syndication accredited vs/non-accredited investor thing (if I'm understanding it correctly) seems to be a huge hindrance to actually raising money from average (non-wealthy) people that would normally be the kinds of people I'd come into contact with.