David - Thanks for the advice. It's pretty much what I've been thinking. We're going sailing with some friends on a 44' Mason this Saturday, and that may help nail down just how big we want to go. A large part of this is still deciding how big we want, and how nice. A part of me says that with our lack of experience we can't pick the perfect boat at any price, so get in for as little as possible (C27 at <$10,000). I know we can get in for even less, but we have a candidate boat in this range that looks to be well cared for and only really needs new bimini canvas. Less expensive boats would need a lot more work. The other part of me says to dish out as much as possible for a boat we'll be thrilled with (and has all the accessories and canvas that we want with no upgrades), take good care of it, and we'll get most of our money out of it if we still want something else after a few years.
I've emailed an old friend whose brother is a broker who has bought and delivered sailboats all over the country. I'm waiting to hear back first, if that does not pan out I'll look for a local broker.
Last edited by TakeFive; 11-10-2009 at 10:06 PM.