I third the "a newer boat is not necessarily problem free" sentiment. I have a friend that bought an 07 because he was tired of fixing things on his older Ranger that he had forever. The warranty company for the new boat went into bankruptcy and was taken over by the state and he had to try to get reimbursed for the problems and he had nothing but problems. The electrical system never functioned properly. The AC had to be replaced and then the boat nearly sunk in the atlantic with his family on board after something with the shaft log broke.
Also the money they are asking for new boats is pretty staggering and I don't like the styling of them. They just seem plasticky and gimmicky. But that is a personal opinion.
IMHO you are better off doing as much of the work yourself and learning as much as possible about everything on the boat. At some point something is going to break and you will need to get it working on your own or find a workaround. If you have a new boat then you are not going to have much incentive to poke around and see how things work.
If you refit an older boat you can put whatever you like into electronics and systems and have an intimate knowledge of how it works. You may end up spending as much as buying a boat with all the same things but at least you know something about it.
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30' Islander Bahama