I don't have a 208 but do have a 2004 GW 228 Seafarer and it seems like just about any boat out there that it's always going to weigh more than you think, or what the advertised dry weight of the vessel is advertised as. Per the Grady White website, it says that the weight without the engines is 2,900 lbs, or at least for a brand new one, and a Yamaha 150 hp outboard is 478 lbs dry, again at least for a brand new one. Even if you look up your exact year of boat though, being a 2006, it still shows on the brochure that the dry weight is 2,900 lbs as well. Which will put you at almost 3,500 lbs for just the boat and motor and before anything else like people, fishing/safety gear, ice, food, beverages and any other accessories you might have. Also, per the Grady White website, they have "performance data" on fuel economy of your boat with the Yamaha 150 hp outboard, and their weight as tested for that test boat was 4211 lbs. Now I don't know about you, but if that's the weight that they tested their test boat at and it's only 200 lbs shy of the max trailer capacity, then I'd definitely want the larger trailer. Because they're probably trying to get the best fuel economy numbers they can get and will likely not have a full fuel tank or other things that will just add more weight to the boat. That, and I wouldn't want to be less than 200 lbs away from your max trailer capacity and have to worry about there being an issue. What's the difference in price between the two trailers? I'd think spending the extra money, which I'm sure isn't going to be a ton more, and have the added peace of mind would be worth the extra cost.
Grady-White 20-foot walkaround cabin Adventure 208: Easy to use walkaround style and a SeaV²® ride. Secure platform for fishing.
www.gradywhite.com