Honestly, as 1/2 of a young cruising couple (with a 30 footer) I would have to say buy either of those boats, and sail the heck out of them, but stay within sight of land! The trips you are thinking about are not easy, and will require a refit of any older boat. Once that has been done you will find you have more money in the sails, rigging, paint, electrical, diesel than the boat as a whole is worth. Either buy one now, sail it, learn and grow with it or buy something that is truly worth dumping money into. In the 30 foot range, based on my experiences looking for the right boat nothing at less than 20k was suitable... Of course, there are always those that make it amazing distances in boats most people would consider unsuitable. Just make sure you have your priorities figured out. I agree with jimmy, IOR boats wouldn't make my top 10 list for cruising.
BTW: About dreams and cruising. My cousin and his GF were dead set on buying a boat and sailing from Frisco to Hawaii. His sailing experience was a sunfish and hers was nothing. He agreed to crew for me from Frisco to Sitka. About 3 days out he started freaking out telling me he couldn't take it etc etc... so Instead of sailing off shore I changed plans to bashing up in 2 days coastal stretches. Pretty sure he isn't going to be passage making any time soon. Along the way I also met more than a few cruising couples and families, all in well appointed yachts that were quite disillusioned with the whole thing. Spending 2 weeks, sometimes in misery, to make the same distance you could drive in 2 days doesn't appeal to a lot of people. Get a blood test to make sure you got some salt in there, or at least don't put all your eggs in one boat so to speak. I'm just about 3 years ahead of where you are in this process, so keep in touch.
Last edited by sailboy21; 04-09-2008 at 02:41 AM.