A couple of comments come to mind...
- You said you have no ocean experience. Do you have
boating experience?
- You're looking at motorboats. Do you have mechanical abilities and can you do all
maintenance and
emergency repairs to a
diesel engine on your own?
- You said "Caribbean". Do you mean anything further than the
Bahamas?
As a general
rule, you should probably spend a fair amount of time
learning about
boats and trawlers. The
boat you think you want today is probably not the boat you'll really want when you know more about them. It isn't that any of the boats you listed are bad - it's just that I'm sure there are many, many things you haven't even thought about.
A couple of other very important questions to consider:
- How long do you think you'll be on the boat at a time?
- Do you mainly want to stay at
marinas or will you
anchor out?
- How many people will be on the boat?
To answer your questions, yes, there are "buddy boat" link ups when people are going to the same place to travel in groups. Some people like traveling that way. Some people hate it. Like everything you'll find with larger boats, it's all about tradeoffs.