PhD in Engineering. So that can be looked at a lot of ways.
And....fwiw... I have my boat in Salem Harbor/Marblehead side and drive about 50 minutes to get to my boat from my house (which is in Needham). It would have been closer for me to moor the boat in Boston Harbor or a little south near Hull/Weymouth etc. But when I applied the sailtime equation, things were better for Marblehead. Had I been in Boston Harbor, I really couldn't be sailing until past the Airport because of all the ship, ferry, PB, and sailing school traffic. If I had been in Hingham Bay (Hull/Wemouth) it is very shallow so I would need to motor a lot to get past Hull Gut.
So even though I drive 50 minutes, once I reach the Village st launch dock in Marblehead, it is only another 5 minutes or so to the boat on the launch, 10 minutes to prep the boat and leave the mooring and then 5 minutes to a wide open Salem Harbor.
I think your list of boats for consideration is a good one. I'd stick to the 30+ foot range for a family of four and a dog.
One more thing - Gloucester: The Annisquam is shallow at low tide. If you're serious about Gloucester, keep that in mind when looking a boat drafts. Also, the Blyman Canal bridge (in/out of Gloucester harbor to Annisquam River) is VERY tight and opens every 15 or 30 minutes I think. Maybe think about a club/mooring actually in the harbor instead of the Annisquam if Gloucester is for you.