When we decided to get a boat it was determined up front that we weren't going to trailer it. Too many hassles, too many unpredictable delays.
In my case, I ended up buy a condo for access to the marina, and also a place to store a vehicle in the winter. Our setup is valet service, though we could also rent our buy a slip if I really wanted to go all-in.
You can always keep your trailer and pull your boat out if you want to go someplace else, but if Winnipesaukee is your primary boating lake, I think you'd be best served with a permanent spot on the lake (valet, wet slip, whatever). Many of the marinas also have their own sort of community, so it's a good opportunity to meet more people.
We're on Paugus Bay, which personally I've been very happy with. There's a few options for gas, a couple of options for food/drinks by boat (Margate and Naswa), ~ 35 minutes to Meredith and really not that far anyplace else (60 minutes to Alton Bay/Pop's). Additionally it's very easy to get to and a short drive from where you are.
I think you'll find that you'd be inclined to use your boat more if it was more accessible and less hassle.
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