First, not last
This may be a first boat, but probably not your last. The dealer knows that and he wants to sell you the next three boats too. With this in mind, and the good reputation that the dealers all seem to have on this Forum, I wouldn't worry too much about buying a used rental. It's probably in better shape than a boat that was just traded in.
As you make your deal, I wouldn't dicker the little stuff to save $100. Look at what costs you a lot, but costs the dealer little: Winter storage, shrink wrap, winterize, dewinterize, spring launch, maybe some extra canvas work to be done over the winter. There's lots of stuff in this life besides the purchase price.
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