No personal experience with it but I have heard from quite a few people that Jacksonville is not the most boater friendly place in the world.
I agree about the smaller is better. My 30' keeps me plenty busy with the laundry lists of tasks and improvements I am trying to do. My boat is a weekender so the systems are very simple as well. If things were more complicated I am not sure I could keep up and I don't really work that much and have help from the girlfriend keeping things together.
If you do buy something and you are planning to do some serious remodeling do it before you move on because it doubles the work to do it while you are living on the boat. I learned that pretty quick and both of us agree that the next boat is going in the yard and we are getting an apt for a month.
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30' Islander Bahama