Is your main goal what you said here, "...to see if I'll use it more or if I should sell it"? If that's so, then I don't believe a three hour+ round trip drive will help you to figure that out. I noticed some Winni slips advertised here in Classifieds on the southern part of the lake, I know nothing about them but at least they'd be closer. Otherwise I'd vote for leasing the slip on Winnisquam. If you decide to keep the boat after this summer, then next year you can reevaluate which lake to choose. Good Luck!
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