I'd take Lumpty's route. Have done that many times and yes, some of the CT cities are a PITA but are preferable to NYC any day.
Ignore the people who think you are making too much of this. You aren't. I have the utmost respect for people who admit they are squeamish in certain driving situations. You aren't weak-you are pragmatic. I lived within 30 miles of Boston for the first 57 years of my life and learned to drive in and around the city. I'll tackle just about anywhere but unless I had no other choice I would avoid NYC.