Nice little write-up. I wonder if we all don't start out that way?? Same thoughts, perceptions, etc.
If you have followed this forum at all, you will know that boat selection is a VERY biased and debated subject... almost as much as ground tackle and electrical techniques.
I typically help work the boat show for Catalina, but I am in NO way connected to them. I do it for fun and to help point people on... and because I enjoy talking to people like you. Some people I point to a Catalina, others I will point to other boats. I am not an expert, but have been there a bit. That being said, let me respond:
There is NOTHING wrong with a Catalina, Beneteau, or Hunter. They do have their place. They have that thing that they were made for and good at, and they have that thing that they were not made for and are not good at. If you primarily are going to limit your offshore work to 3 days (maybe a little more, depending on the boat)... but will primarily be going from island to island... in my opinion, THEY ARE THE BEST BOAT. Better than a Valiant or several of the others mentioned. They are big and fat and roomy. The term floating condo is not far from the truth. But this is NOT a bad thing. This is how 99.99999999999999999% of people ACTUALLY USE their boat. I have been on MANY Valiants and other blue water boats. They are small and tight by design. 5 days at sea with pounding waves will really play havoc on coastal cruiser (Catalina, Hunter, Beneteau, IP), but not (hopefully) a good bluewater boat. But when you drop that anchor... well, the Catalina is SURE going to be a LOT more comforable than that tiny little Valiant 50. Rememer one of the few truths of cruising, if that is in fact what you will be doing: 99% of your time is anchored, 1% is going. Now, where is that 'going'... that is what you have to answer.
Everyone dreams of sailing the great barrier reef, blue skys offshore, the sun setting over the Red Sea... but the reality is that most people never do it (even the ones that own the boats that can). There are too many reasons for this to intelligently discuss here, but in my opinion (knowing many of these people), it is because:
1) They found the islands and the things on this hemisphere more beautiful than expected and more than a person could see in a lifetime. Why leave it?
2) Offshore can be really ugly... and the enamour of it wears off after the first 24-48 hours. It is not 2 or 3 or 4 days to Australia or Hawaii... try a couple of weeks or longer at sea. Once you are about 100-200 miles off the west coast, you are out of sight of VHF and any timely rescues (if any at all) and any communications (without SSB/HAM or Sat Phone). You are on your own with no place to duck and you WILL weather whatever nature throws at you... including TD, TS, and Hurricanes (God Forbid, but it does happen). This might not sound so bad sitting in your chair and reading this... but when you are faced with mountainous seas and no one to help... well, that changes your perception.
3) Their boats are uncomfortable. You are just going to have to go aboard a V50 to understand what I am talking about. My Catalina 400 is bigger than a V50 in comfort and space down below. PS, I am a fan of Valiant's... do not take this the wrong way. I know the people there and have nothing but respect for them, their boats, and their service. If I was going to do a circum or really long offshore, it would be at the top of my list. And they really are not that expensive (compared to some others).
Let me ask you a question: Does Lexus make a better product than Ford? I bet you just answered yes. Now, let me qualify that question: If you own a farm and need to pull a trailer, does Lexus make a better product that Ford? Well, maybe, but no way in Hell you would take a Lexus over a F350. Get the point?
I know you have read some threads about people putting down the production boats (especially Hunter) and some of that IS deserved, and some of that is NOT. Valiant's are made better than Hunters, but it would NOT be my choice if I was going to be island hopping. If I had to choose between Hunter and Valiant, even if they were the same price, I would take a Hunter every day of the week and twice on Sunday.
You are new at sailing and have probably not done much offshore work. Go buy a production boat (coastal cruiser) of your choice and hit everything you can in this hemisphere. They will be comfortable and you will learn a lot. Your wife will like the space and how much she can spread out like she was at home. If you ever become so bored that there is nothing left on this hemisphere that interests you, go trade your boat in on a Hylas or Valiant and push off from there. Or better yet, go pay Dockwise to ship your boat to Australia, save a few hundred grand, and avoid getting the crap beat out of you with three weeks at sea.
Just my opinions.