The old real estate saying is *drive until you qualify* - meaning - how far are you willing to commute to work, so you can get the house or apartment you can afford, and like? I you can nap or read or do computer work on the train every day, then see how far out Metro North or Amtrak ( far more expensive) go, in the direction you are looking. I live less than 100 miles north of NYC, and have neighbors who take the Poughkeepsie or Rhinebeck trains in every day, or can telecommute a day a week. As you get train stops closer to NYC, your living budget goes up as your commute time goes down. We often drive to NYC fro shows, concerts, games - but even do that less than we used to, because the trains (and there is also a bus - not our first choice) are far more convenient - and we now get Senior prices.
If your work would allow you to live AND work further north, then by all means check out places in the Hudson Valley. We have been here 45 years, and have no intention of EVER moving - although we do travel a lot now that we are semi-retired.