My advice is that this sort of thing is much easier when you’re earlier in your life journey and career. It’s fun in some ways but the travel will wear on you. I spent a few years flying in and out of different cities for meetings and the logistics are very difficult. I am very glad I don’t do that anymore. That said, you get to experience two cities with the same job.

I have had colleagues with similar arrangements and they seemed to be constantly coordinating pet sitters, child care, but if that’s not where you are, that’s not an issue. Being out of town a lot is hard on your partner, kids and pets.

I would push a little bit to see what the job flexibilities are, like if you could do one week in person, three at home and stuff like that. I’m sure they have other employees doing similar things.

Regarding plane or train, I would personally take the Acela because you can walk around en route, the internet is ok so you can do work (but not video calls), and don’t have to check bags. You walk on, walk off. The airport is a drag and it’s a lot of logistics just to get from the airport in NYC to your office.

Good luck!