I'm in the market for a bluewater. Used to have a cal 25 for years and sailed around in Galveston bay until I moved inland and sold it. I've been reading forums like this for awhile doing research to see what my next boat should be and have seen the question of "what bluewater boat to get," and "what makes a boat bluewater" etc.
I found this and regged just so I could post it. If you're asking those questions, then you should read this --an amazing story that adds to the answers for such questions. Just look at the things that went wrong!
EQUIPPED TO SURVIVE (tm) - Lessons Learned: Sailing to Hawaii...The First Attempt by Arnold Rowe
I take some much from a story like this, from "make everything heavy duty as possible," to "have backup parts for items you can't move without," to "double check that everything works!" to "do drills with gear to make sure it works in a pinch" and the list goes on.
By the way, because of forums like these, I think I've narrowed it down to one of the heavier boats like an Alberg based on my budget. Thanks to all those here for the wealth of info.