We just bought a 25' Outrage. Money was/is definately an object for us, but since we were willing to ship from anywhere on the West Coast to where we live in Alaska, we were able to expand our options.
Some of my criteria were:
Minimum of 17'
Internal fuel tank(s)
Cabin(size, not an issue, but survival in bad weather - big issue here)
Chime needed to be such that we could take moderate seas
Ability to hold lots of gear since we camp, fish, hunt, dive etc.....
Needed a trailer so it can be maintained at home
It seemed there were always trade offs when looking at boats, bigger cabin, means less deck storage area. Small and easy to tow, means less usable space and not so good in foul weather.
If you're serious about buynig a boat I would write down what features you want and start searching a lot of differnet places. Try not to limit yourself to just the local classified ads. That's where the internet saved us a ton of money. We shipped our boat up from Washington and when we re-sell it here in SE Alaska, we'll be able to make up for the shipping cost and more.
Since I havea Captain's license and drive boats for a living(sometimes) I come across a few that I thought were outstanding. One feature I do like for loading and unloading is the drop bow. Makes getting out of the water a snap too. Just make sure the thing never comes open while your running!
Boston Whalers have been a staple here in Alaska for decades, but the aluminum drop bows are gaining in popularity every year.
If I was back in California and diving the Channel Islands and staying on the boat, I would vote for something like a Skipjack. Everyone can come inside for the ride back to the mainland and stay warm, you can cook a hot meal, use the restroom etc.
