It looks like you are doing some amazing work! 

I can also point you to a ton of resources if you'd like to do your own research.

If all parties were agreeable (and would likely agree on an interest rate lower than a bank's would be), with $0 down his monthly payment would jump $300-$500, but now he would be building equity in the property.Is there anything else I should tell him or anything I am missing?

Any thoughts on a transaction like that?

I would like to find a lender that would base financing on rent/income.To answer your question, the property is fully occupied. 

Also, keep in mind that some aldermen have opted their wards out of AirBnB and the like as a blanket ban.

Good beaches around as well.

Since each of your LLCs owns 50% of the holding company, but the holding company doesn’t own your individual LLCs, the IRS will likely treat your LLCs as separate, single-member LLCs for tax purposes.

If I send a LOI (Letter of Intent) do I still need a representative like a RE Broker for residential properties? 

I feel like my best route to getting started is by working with partners or private lenders given my current available capital.