Just from the little you wrote, it's pretty heavy on the red flags. 60 days on the market (depends where this is whether that is a lot or just fine, but definitely overpriced at this many days) plus no sold comps.

Please note the information provided below is a layman's definition designed to provide a basic understanding for the general audience.

It definitely escalates the situation though, so I'd research the process and carefully consider the option before embarking on it...but if you pursue that route you can likely escrow Dec 1 rent and I'm sure that will get some attention. 

Guests on VRBO never question this because everyone on VRBO does it.And I think @Alanna Schroeder advice is definitely something most off island owners don't think about.

Fast solutions have slow problems.This definitely includes any risk-on investment.

So percentage wise Jacksonville has seen a crazy amount of new supply being delivered which has affected rents.We also manage a portfolio of new construction homes in Palm Coast and Palm Bay and rents for those homes have dropped $25-75 depending upon floorplan and submarket and they’re taking longer to lease up compared to 2 years ago.A lot of Florida is having similar issues of stagnating or dropping rent, but it definitely depends on market, submarket, asset type, etc. 

there are definitely states that require MLO licensure to do any loan on a 1 to 4 unit.. about 15 states require it .. the others dont as you suggest.

If you're going to self-manage you should definitely pick market(s) that you are familiar with.

To do a "boot-camp for syndicating" would be definitively stepping over dollars to pickup pennies. 

You should definitely look at investing out of state.