Naturally, we would like a low maintenance, easy upkeep, safe boat which I guess is the implication above by going with fglass. However, can you name or point the way to one that is a true proven ocean crosser?
Nordhavn.
This has been an interesting thread to read. I can't comment from experience on the pros or cons of wood boats as I've never had one nor had anything to do with one. Well, one, a girlfriend's father's 16-foot, locally-built outboard cruiser and taking care of it was a royal pain in the ass.
From participants on the Grand Banks forum who own wood GBs I know these boats can be a lot of work, can cost a lot of money, time, and effort to repair.... and can be very rewarding to their owners.
It seems obvious that you both have made up your mind to do what you have been describing--- buy a large wooden boat for a relatively low price and attempt to make it work for you. While the experiences related by people on this forum who have had extensive involvement with this type of vessel seem to me to be something well worth paying attention to, the impression I get from your responses is that you are going to do this, or at least try to do this, regardless of what anyone else might have to say about it.
So perhaps you should just do it and see what happens. Asking incessently for advice you don't seem to want to hear would seem to indicate that the best way you're going to learn if your idea is good, bad, or indifferent is to just go do it.
Second guessing the results of something that hasn't happened yet seems rather fruitless in this situation because of the staggering number of variables. From your comments and questions you both seem awfully close to the bottom of the boating learning curve. The numerous comments and suggestions from people in this thread who are near the top of the learning curve that the best and safest way to ascend the curve is to start with a smaller boat do not seem to be something you are willing to consider.
So it would appear, at least to me, that your best course of action is to roll the dice, buy a big wooden boat, and see what happens.
Prior to writing this post I had just finished reading the articles about the Bounty testimony that were linked in Charles post in the thread "Bounty-- sinking hearing by USCG." Reading about the incredible incompetence, inexperience and poor decisions that led to this tradgedy seemed to have a rather eerie potential connection to this thread.
So I dunno..... If what you want is an afirmation that you are approaching your dream the right way, I'm not sure you're going to get that here, at least not from the people who have to some degree or another gone down the same path themselves in the past. So if what you want to do is really a critically important dream for the both of you to follow, then perhaps you should simply stop asking for opinions and just do what you want to do.
Whether the course you take is right, wrong, or somewhere in between will become apparent soon enough as you learn whatever lessons reality has to teach you.
So if you look long enough will potentially gravitate to certain kinds, size, style of boat. Its out thee you just have to define and find it. 
