Don''t write the check yet, James.
Having "used" break and discovering "new" right in front of you makes you want the "new". But it will be an emotional decision ("<em>This one</em> won''t break!"). You were indulging in a tangible day-dream at the boat show, but that doesn''t mean you should buy a new boat, no matter how emotionally satisfying it will be in the short term. Once you wake up from that dream you will find yourself with a quickly depreciating boat and a monthly note to pay. Your only consolation will be to say to yourself, "Well, at least it won''t break."
Cool down, take your time, look around, and be honest about what type of sailing you''re likely do here on the west coast. It''s apparent that you have greater ambitions than your 20-footer can manage, but what will the next chapter in your sailing career look like? A lot of coastal cruising and island-hopping. Maybe make it up as far as Canada, or down as far as Mexico. But crossing oceans? Not likely for now.
I''m pretty much in the same spot. Sure, I dream about crossing the Pacific to Hawai''i (and then Tahiti, and then...), but I have to be realistic. My next boat will be a 30-footer (or so), will let me coastal cruise single-handed, and is probably sitting in a marina on the west coast right now. Take a look at the boats slipped in Ventura: not many Tartans or Island Packets, but plenty of boats by the Big Three (and similar makers) that are providing good service to their skippers after years of sailing and which are willing to give you adventures for years to come, at a price that you can live with. One fundamental trait of a good sailor is that he makes sensible decisions.
I still dream of being Joshua Slocum. But then when I wake up, I see there are many places that I haven''t discovered yet, right along this coast. And that''s where my voyage of discovery must start.
Hope this Helps,
P.S.— I still want to hear about your cruise to the Channel Islands: sounds as if you had at least one adventure with your rig