Spring is always the time. That's when the boat shows are going on and most new boats are sold. Those people buying new have to sell their boats first, and that usually means a pretty good supply of used boats on the market. You'll have the most options in the spring, but maybe not best deals, prices can be hit and miss.
There is also a window around early September, where guys who know they have a new boat coming in the spring (Pro Staff, Dealer demos, etc...) are looking to sell their current year boats. That often creates a trickle down effect of people looking to sell their boats and upgrade. It's the end of the season too, kids are back to school, holidays are over, and there's always the guys that know they're selling and just don't want to have to store the boat all winter long and deal with another year of depreciation. If I was looking for the best price, that window in late summer/early fall is what I'd be focused on, and the closer it gets to freeze up, generally the better the deals get.
Know what you want (it sounds like you've done your homework), have your cash in hand, and be ready to travel. When the really good deals pop up, you have to be ready to strike, because they go FAST.
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