I'm thinking of buying a C-Dory, specifically, and am wondering what the dealer's wiggle-room is.

Fleas won, eh ?  

There will be a hell of a sale on used boats down in N.O. soon.  Insurance companies will total many of them.  Watch ebay.

could be quite a bit. Pay what you want to pay, and have later regrets that you should have offered even less for it. Remember you may need maintenence from the dealer in the future, so a good relationship is important. Even if you do most of your own work there is usually a few items that will need tending during the first year, though the boat you are looking at is pretty basic.

I buddy up to the local Yamaha guy here so he doesn't charge me full pop for oil, plugs and filters that I buy over the counter.

If you are buying a NEW boat, I always recommend waiting until the big boat shows that go on in the winter. The markdowns on MSRP will blow your mind. It is not unusual to find deals that are 30% below retail. The manufacturers give the okay for huge incentives during the shows.

I know guys that buy a new boat every year at the Atlanta Boat Show, cruise all summer on low, long term payments, and then sell the boat for what they paid for it in the fall.