I optimize miles too but, for short distances, it's mostly not worth it. For Boston to NY I essentially always take the train which is more comfortable if not necessarily faster. And Amtrak points are probably actually more useful for me in general than airline points. I'd get 500 points on United and use of the lounge but, really, that's not worth a whole lot. Amtrak is already basically as comfortable as an airline upgrade--which is hard to get on a weekday peak travel slot.