I can fully understand where you are coming from, and I think a slip is probably the best bet for you, especially if you get a boat with sleeping accommodations.
That said, I have a boat with sleeping accommodations and I cannot imagine having it in a slip. I LOVE taking it to different lakes, rivers, and the ocean and trailer towing does not bother me at all. If you have an adequate tow vehicle, consider towing a bigger boat for awhile before you opt for a slip.
Winnipesaukee is wonderful and I'll always keep coming back, but man, it's very limiting (geographically and legally) compared to all the other places you can go in a boat. We live in trailer boating paradise. The ocean is less than an hour away. The Great Lakes/St. Lawrence River are only a 6.5 hour drive. Lake George, Lake Champlain, Buzzards Bay, and the Hudson River are all only 3 hours away. Narragansett Bay, the CT River, or the Lakes region of Maine are just 2.5 hours away. All of those alternative places allow overnight anchoring.
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