So im trying to figure out based on my situation what is the best move for long-term financial sucess.Now the rental is bringing in $800 net cash flow monthly, after all expenses are paid.

Same as Collective Mastermind with Ken Mcelroy, Jason Hartman, and George Gammon....cuz that one is wicked expensive, but I'm strongly considering it. 

Quick list, pros- low vacancy rates, high rents, moderate/high home appreciation, high rents increases, demand is always there as people move/commute from NYC; cons- very competitive, pro tenant laws, high property taxes, some towns have rent control, high barrier to entry with expensive multifamily prices. 

We finally found an excellent broker, he's not the cheapest but not the most expensive, but he is very responsive and is always looking for ways to save money.  

I have always wanted to live in a warmer climate (ideally closer to a beach) but these properties tend to also be expensive and are better for appreciation than they are for cash flow.

I assume metal roofs in general are more expensive so thats why builders, flippers, roofing companies push them because they are better for their margins, but if you are planning on holding the asset for the long haul I have to think metal is going to last way way longer. 

You are making almost everyone more complicated and expensive regarding banking and tax preparation. 

It is a matter of if you want to hire them full time on salary - if so hire as employees, but in 90% of cases, you can just pay them as a business expense with a contractor invoice

But he is expensive.

Collin, I don't want to discourage you and I am just looking out here, just be mindful that you would be going into it with 5% down payment and underestimating building expenses could be very risky.