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I have pretty much narrowed my boat search down to a new 32 outrage, but still have two lingering issues: first, I am constantly hearing on other websites about how 'horrible' and 'rough' the ride is on BW's- is this really an issue, especially with the newer, higher deadrise models? Second, I have read a number of 'reviews' for BW's stating that water infiltration into the transom (and thus wood rot) is a common problem- how 'common' is this problem, or is it just bad press?
Bad press on both accounts. I have ridden in a 32 Outrage and the ride was smooth and not rough at all. I do suggest you get with a dealer and take a few rides in different sea states just to be sure. Disclaimer, I am comparing to an 18 foot boat, so if you regularly ride in 30+ foot craft, you may have a different opinion.
Water that gets into the foam or wood is an issue, but if holes thru the gelcoat are properly sealed, you should have no problems. If you are looking at a used boat, I would have it surveyed just to be sure.
Of any Whaler ever built, the 320 Outrage is the last one anybody could call "rough riding". That is total hogwash. Sea trial one yourself and you will see what I mean. There are a lot of sour grapes out there among those who cannot afford a Whaler. You may as well get used to that sort of criticism. Whaler owners have heard it for almost 50 years.
The comment about the Whaler transom is also way off base. While a lot of manufacturers use plywood in the construction of their transoms and suffer rot and delamination because if it (Grady Whites c. 1990 were notorious for this) the plywood transom of a Whaler has a surprisingly low rate of failure. I have never even seen one personally. I attribute this to the unique Whaler UniBond construction process that encapsulates the plywood in pressure driven fiberglass resin and polyurethane foam. There is no way air can get to it even if it is wet and thus rot is extremely rare.
I got a trial on a 320 Outrage (twin 300 Verados) last February at Miami's Boat Show. The temp was in the low 50's and since i come from the tropics, was a little affraid of getting wet in those conditions. Regardless, the ride was sweet and the boat ran like being on rails (no pounding, impressive tracking and very stable on high speed turns). The trial lasted about 15 minutes and despite the heavy traffic in the water and a lot of wakes coming in all directions, i never got a single drop of water on my sweatshirt.