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Bud,
I think the very first thing to do, is decide what you want out of your boat. Just fishing, fishing/cruising, inshore vs. offshore. This is the best starting point. What are you looking to do?
Second, come up with a figure that you can live with... don't forget to include fuel, storage, maintenance, etc. (and time... how much time do you want to devote to upkeep).
There are so many factors. Myself, I wanted something I could store in my garage, easy to trailer, easy to launch, quick cleanup, easy on gas. I also prefer light tackle fishing and aspire to do a bit of flats-type fishing locally, on the cape and over at Nantucket where I vacation in the fall. I live in Weymouth which makes Boston Harbor my home waters. I came up with a 17-18' center console w/ a 4 stroke outboard. I looked at a bunch and attended the boat shows.
I found a great deal on a boat that fits nicely into my life. I figured it would be a really good starting point and I'm really happy with it and I put a heck of alot of fish in it this year.
I think if you're going to buy a boat, the most important thing is to match it to your style. You want to make sure you can and will use and enjoy it as much as you can or its not worth it. If you want to trailer, don't buy a big @$$ boat that's a pain to trail and launch. You won't do it on those days when you're up in the air about going. I know John wants access to Block Island and other offshore venues, so he wants the big water performance. As Van said, he likes to take out family and friends and likes to cruise around as well, so he likes the cabin of the walk-arounds.
I've only had the boat a season, so I wouldn't give any recommendations, but the size, power, etc. have worked out perfectly, so I'm glad I went through the whole thought process.
Good luck and have fun with it. I love going to those boat shows and checking stuff out.
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