Since you are renting, taxes won’t be as big of a deal then if you bought, so you might want to look at the Black Rock section of Bridgeport. Definitely has a social life that is walkable. Can walk to a train station. If you are hung up on the taxes, then look at Milford. Also consider when would you be driving to either Fairfield or New Haven, you don’t want to be stuck driving on 95 to Fairfield in the morning!

Absolutely right. I was once behind a state trooper who was suddenly put on his lights and began this maneuver on 95 between Bridgeport and Stratford. When he came to a stop, blocking all lanes, he got out and dragged a chair to the side of the road.

If you enjoy hiking and looking to meet people, there are several Meet Up groups that focus on hiking. Great way to explore with people who might know the trails and get to meet people. As for living, first you need to decide what is important to you. Shoreline? Rural? Hi density housing? We have it all within a few miles of downtown New Haven.

You mentioned “one of the colleges”, so not necessarily Yale. Depending upon which one might make a big difference. Any school, other than Yale, you will want your car, so parking becomes a factor.

There’s a number of meetup groups where you might find people with like interests.