Hivolt,
I think a 30 footer with twin engines is easier to dock than a 25 footer with a single engine. That said, neither is terribly challenging. I'd be happy to teach you to dock if you want some instruction.
I highly recommend getting something you can tow and spend multiple nights aboard. My wife and I tow our 25 footer all over the north east and have a blast exploring new bodies of water on 2 to 7 day trips. Winnipesaukee is our "home lake", but we've cruised the Hudson River from Saugerties to NYC, Lake George, 1000 Islands, Southern Maine and NH coasts, Chesapeake Bay, Potomac River, Lake Champlain, Narragansett Bay, and Sebago/Long Lake/Songo River (multiple times). Outside NH, you can drop anchor and spend the night anywhere you want. It's fantastic.
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