buying first boat
I am glad this thread has been helpful. I think you got a great reply from Tsenator who has mentioned the smaller/newer more production oriented option.
I looked at a very wide range of boats, and got some good and generous advice from quite a few people, including folks in this forum. All boats on my short list fit my objective criteria and having that as a cut off was very helpful. The choice came down to the subjective factors I listed and my own personal bias. In the end I decided I would contribute more towards the boat and so my list shifted dramatically. I made a decision that an aft cabin, the quality of the joinery and the bluewater reputation of the boat were important to me and that I would spend more to get those qualities that I was looking for.
Invictus is a Wauquiez Hood 38. A pretty well respected Ted Hood design, wonderful cabin, yacht-like joinery and a very seaworthy.
I could not be more pleased with the boat, it was a very good choice. But in reality, I could have spent less and gotten a boat that would do essentially the same for me (although my long term plan is for substantial bluewater cruising). It really was a matter of budget.. but if getting a more expensive boat meant NOT taking off for the islands... my advice would be to go for the less expensive boat and go for the islands.
Hope this helps.