First flight to JFK from BOS is usually in the gate by 650 and he last on leaves JFK at 2250 with a ton in between plus 2 hourly shuttles to LGA. In the 4 years I've done the commute to JFK I've had to spend the night in NY 4 times, and I am not senior.
Commuted to DTW for a couple months. It's not bad, but much more limited. People who complain about the BOS-NYC commute have never had a real commute. This one is simple.