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I doubt you can find a safer, better outboard cruiser/fisher than one made by Boston Whaler. Unfortunately it follows that the boats are among the pricer brands.

If resources are not a problem a new boat is always fun although with a cruiser and it's more complex systems such as generator and air conditioning the first couple of outings can be a little frustrating. A good way to reduce the frustration level is to have a long and thorough shake down/delivery cruise with a dealer's rep. Ask for a demonstration of everything even if it isn't used on the cruise. Make sure you know where every valve, switch and breaker is located and how it operates. This applies to used boats, too.

I would look for a lightly used late model Whaler that meets all your requirements before spending for new, but our resources are limited.