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My wife and I recently went through this same process and it didn't end up the way I thought it would. I sold my 19' center console in '07, thinking we would quickly move up to something in the 23-25' range.
With things going on with my kids' activities, my mother-in-law's health, work, etc. we didn't really shop for another boat in '07 & '08. In the mean time, the boat market has tanked and there are lots of good deals out there.
I thought for sure something like a 23' pilot house or walkaround would appeal to my wife, but after re-evaluating what we really wanted in a boat we decided to stick with another trailerable center console and only moved up in size to a 21' boat. We closed on the new boat in October.
The new one has a very useable head in the console and a T-top which makes it a bit more user friendly than the previous boat, but my wife had no interest in a cabin.
It's a great time to be buying, not so good to be selling. Good luck!
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