On the subject of driving 3 hrs twice a week vs a 30 minute flight, how difficult is it at most regionals with NYC bases to hold trips that have early shows (6 AM or earlier) with late finishes (9 PM or later)?

I live in central CT, which is 2-3 hrs from all 3 NYC airports, so of course I want to absolutely minimize my time in the horrendous traffic, so getting early starts and late finishes would be ideal.

I'd gladly sacrifice some weekends and accept less dense trips to minimize traffic in and out of NYC.