Re: Pitfalls of trading up?
Good thread to see, especially with people really recommending selling your current boat first. I'm on a Pearson 323 which is an amazing boat for me for the next several years, but wouldn't mind trading up to a Tayana 37 for blue water cruising once I've done the Bahamas a couple times. My current boat is perfect for that area.
My main worry with selling the current boat first would be that I'm living aboard it and would worry that it might have that messy lived in state. But I guess you can always just be real disciplined about keeping it clean for showing and move a lot of your clutter out.
Also there'd be some things like my kayak, kayak racks and wifi system I'd want to take with me since I'll want them on the new boat and the resale value on them is nil.
What I'm finding really hard is keeping from upgrading my current boat more. Trying to balance new systems/comfort items for the current boat(I'll be in for several years yet) vs knowing that every dollar sunk into her won't be a dollar out on the sale is a tricky balance.