What some fall into is the elitist mindset where they feel need to justify high prices. People see rents in NYC and it then becomes: it's expensive to live in NYC. Actually, that's false. It's expensive to sleep in NYC is more factual. And yes, trains are expensive. But I don't bring my truck or bike up here, why would I? $129 a month and I can go any where in the city. $30 round trip if I want to go to Long Island or the Jersey Shore for the weekend. Can you pay gas, insurance, maintenance, car payment on about $180 a month? I cant. NYers love to complain, but we all know how good we have it.
I think its, like you said, what capacity are you involved in the city that would determine high prices overall. Are you living there, just visiting for a while, bring your car, have kids, etc? All this stuff really matters. For me, as a person still chained to Jax but living for a while in another city, it was def expensive living. But the food in DC, and virtually at any place you go, pound for pound was more expensive simply because of where it was & what the city has become. Dives can be found, but they're not easy or plentiful. High profile places here in Jax (like say Cool Moose) w its cheaper options wouldn't be the same DC & you'd have to really go searching to find it, if you ever did. Any place there that's higher profile is gonna be much more pricey.
BTW, you're correct that NYC overall isn't too bad on the wallet for living when factoring in everything. For what its worth, DC has become higher in terms of rents & overall living expenses than most of NYC (even Manhattan) & you can live better there. I know people who have done both & they say the same thing, as does poking around online & rent shopping. I don't know what's happened, but its sorta gotten out of control. Maybe its the fact that the District is much smaller & not a lot of space to work with, supply & demand, the types of high paying government jobs (or jobs that tie into that) in the area, etc.
I don't know if I'd bother ever trying to live there full time again. Not worth it IMO. And certainly not when you consider that NYC can be had for cheaper, has a train that actually runs everywhere you'd ever want to go & for 24 hours, etc. NYC = World class city that can prove it. DC = Wannabe world class city that wants to go ahead & charge you for it just because.