buying first boat
Jeff has given a nice list that tends to be on the performance side, as he has said that was what he was looking for. His comments on displacement and modern hull forms are very helpful, though keep in mind that in the price range you are looking you are likely not going to get a boat with a true modern hull form. btw, the displacement of the Hood 38 is 22,000 with a D/L in the mid 300''s and it still PHRF''s at 129. Very comfortable and solid in a seaway.
Jeff''s list is somewhat diverse with boats from the 70''s, some slower boats like the Hughe''s, cored hull designs like the C&C and J''s and more. Also, while this is a very nice list, it is not particularly cruiser oriented or oriented towards traditional boats (Jeff is a very advanced sailor). Probably to more important point is that many of the boats on the list will be hard to find or out of your price range.
I would suggest the following resources to wade through all these boat suggestions and info.
First, I would get the two vol set, "Practical Boat Buying". You can find it on Amazon. It is a comprehensive guide to a wide variety of boats from 20-60ft. I found it very valuable for info on boat construction: hull build, hull-to-deck joint etc. Good compendium on boats specs too.
You can find a large listing of boats on: yachtworld.com. Use this to sort through your various search criteria of age, price and region.
Sailnet has a "Boat Check" section that is somewhat helpful with owners comments on various boats. It is owner biased though.
If you really want to see some "back and forth" about specific boats, try searching on Google.com in the discussion groups section. You will be AMAZED at the discussion threads captured. I found it interesting but remember you really don''t know how expert any of those opinions are, though from the discussion much is obvious. I have found it a good resource for looking at both sides of a particular arguement such as cored vs non-cored and info on teak decks and the like.
One piece of advice, don''t travel far to look at a boat. You will unfortunately find that most are in terrible shape no matter how they look online or what the broker says.
Also, as far as size goes... I am not sure how much of an issue it is. Depends on what experience you have. I am assuming you have sailed but just have not owned a boat before. A 38 ft could be daunting to some, while 60 ft is a piece of cake to others. I think that if you have captained a 30ft boat before and are reasonably confident, 38 will not be much of a problem. It WILL seem daunting at first, perhaps even for a couple months... but boat owners tend to learn FAST and you could very well be completely comfortable in one season.
Another issue is that if your goal to move to the islands is set in stone, then buying a smaller boat now (25-30) with the idea of selling it later for the ''real'' boat, you will be set way back in terms and time and finances.
Its really up to you.
Hope this helps.