Lots of options and it def depends on the environment you want as a backdrop, but imo consider: Salem, Plum Island, Halibut Point, almost anywhere in Rockport/Gloucester area, but if you like the rocky coast/lobster fishing village thing check out Lanes Cove (morning is best for low winds and calm seas… and great sunrise obviously), castle hill/Crane estate, Stone tower in Lynn woods, and/or if you have a professional local photog ask them as well. They’ll def have some ideas likely with sample shots of other couples and will know the best times/conditions to hit each spot.

This might help, TLDR: call your town building inspector.

https://merrimackvalleymarealestate.com/legal-definition-bedroom/

I’d talk to your new employer about this maybe? I’d bet there will be carpool options from most nearby towns, especially if it is a larger company. Having said that, you’ll get more value for your rental $ in Worcester and it has improved a lot in the ~20 years I’ve been in this area. People still have a dated view of the city imo. Anyway, there are very nice apts within walking distance of the commuter rail and it is 2 stops to get you w/n a couple miles of Hopkinton center. Where you could Uber, catch a ride with a colleague or even bike on nice days. And you can fly round trip from Worcester to JFK for $150 (or less) when you are missing the city. It’s a 30-min flight. I’ve done that a lot myself.

1st offense is just $100 fine (plus court costs if it goes to court.. or maybe a magistrate). No insurance surcharge. But why fight it? Just pay the $100 and move on. And then stop doing it.