Your situation is a lot like mine, and I think the money you save going with the 281 can be used (partly) to upgrade and update the '97. Certainly with any boat this size, a few feet can equate to a noticeable difference when it comes to cabin space. The 281, though, has a good amount of space on the inside, and I have never felt cramped with a few people on board. In my mind, if I ever outgrow the 281, I'll take a bigger leap to something a lot bigger than a 311 or 323. Just my thoughts, but I liked having the funds to outfit her properly after I bought her last year, and I have never wished that I had a few extra feet.