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Have you considered keeping the boat in the water? You can pay lots of slip rent for the price of a truck and related upkeep. Les at EQ has service trailers to haul a boat for maintenance so you can save the price of your own trailer too. You will use your boat more if it is in the water...

You have several interesting questions in your post. To do all the things you want to do I think you need a 22. I have owned 14 boats in all types of configurations and sizes up to 54 feet. Buy the largest boat in the category you are looking at. I own a 22 and never cease to be amazed about...