While my boat is a bit smaller, I don't consider launching and towing to be big obsticles. The time to/from is a bit of a hassle (I'm from your general area). It would be a bit more convenient to leave the boat on a slip but not $3000 convenient for me.
The biggest tow/launch hassle is getting parking on summer weekends on the big lake. I usually go very early so not so bad for me but try getting a spot in Alton (closest free ramp) on a nice Saturday after 9AM.
I like both Squam and Winnisquam but like the size and variety of Winni. Squam makes me pretty nervous with all the hazard though but offers nice fishing options and is a beautiful lake. The ride up there is similar to launching on the northside of the lake (close enough) so if its a distance thing b/t Squam and launches in Merideth, CH or MBB....that would not sway me from Squam.
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