So I live in West Hartford and have done this many times as I had a job where I needed to be in Brooklyn once a week. Plus I lived in NYC for 5 years so sometimes I would go in to see friends.

I have tried a lot of combinations and it’s always rough. My round trip from weha is 7 hours and weekends when I went in to visit friends it was closer to 5.

I recommend maybe living in a town off of route 8 because usually that’s a faster option than 91 to get down to some of the towns with the best train times.

Honestly, you could also live in New Haven because your wife will be doing a reverse commute to Hartford and it wouldn’t be that bad compared to the other way around . However, the train schedule to New Haven is the worst to New York City. I usually go in and out of Darien because of how frequent the train goes through there.

School buses are not always part of the school system. A lot of them are owned and operated by private companies that bid for the opportunity. Trust me - those companies have money. They are bank rolling wedding shuttles, prom shuttles and tons of other events that need transportation.