You indicate that you'll be in the Bay for a while and longer term, maybe going South. I would recommend buying the boat that suits you now. As novices, this boat will allow you to form strong opinions for what you want in a longer range cruising boat. And you will form them. I've been on Sailnet for a while and see a great many people thrash about searching for years for just the right, ultimate, every option included, perfect condition boat (which does not exist). In the mean time, they're not sailing.
I highly recommend finding a broker and let them work for you. In this economy they will work. Guaranteed. I used Dan Nardo at Annapolis Yacht Sales and was incredibly pleased with his professionalism and dedication to getting us into our current boat. I have no relationship with Dan or AYS except as a satisfied customer.
A word of advice - We have friends who cruised from Maine to the Caribbean for 2.5 years on an old 70's Hunter 37. I'm not recommending the brand, but putting forth the opinion that you don't need a "blue water" boat (whatever that is) to do Caribbean cruising.
Sabre 38 "Victoria"
Last edited by Sabreman; 05-15-2011 at 09:14 PM.