Boston to DC doesn't really make sense though unless I've just decided to work on the train for the day so I don't need to deal with the airport (and probably pay more to do so).
Other than that, it's hard to justify train from Boston. I looked at it once to Chicago and it made utterly no sense either in terms of time or cost given that I'm going to get a sleeper on a trip like that.
That's assuming euro-style cities where you probably want to go from one urban center to an other though: plane requires going outside the city (to the airport) in advance due to security procedure, waiting for security and boarding, then at the destination going from airport to city center.
With HSRs, the stations are in or relatively close to city centers (usually easily accessible through public transportation), you can arrive 5mn (or less) before departure, delays may be somewhat less common (though the justification differs e.g. suicides on the track is not an issue for planes) and you arrive at the city center with better travel comfort. Especially for people sensitive to air pressure.
If you want to spice it up, check out Southern Airways Express[0]. You can fly between Pittsburgh and Lancaster for as little as $30 on a tiny little 8-to-10-seat plane, which is a really unique and scenic experience. Catch a ride to the Lancaster Amtrak where there are a lot more options for getting to NYC.
I've done Megabus and Greyhound on return trips. You get what you pay for. But if you happen to live in the North Hills, the bus depot for Megabus is in Ohio Township and if you ask nicely they'll let you ride up there.
The only downside is that it's on a once-per-day schedule (Pgh->NYC at 7:30am and NYC->Pgh at 10:50am). It's 8-9 hr downtown-to-downtown (vs. ~5-6 when flying) so you'd really want to do Fri/Mon for a weekend. FWIW, there are three or four Megabuses per day too, including an overnight bus in each direction, for when the train schedule doesn't work.
Also, flying to NYC from Pgh is oddly expensive, like $400 roundtrip expensive. Amtrak is about $150 RT if far enough in advance.
Anyway, welcome to Pittsburgh! I hope you're surviving the snow...
Absolutely -- IMHO for mid-distance (200 mi to 500 mi or so) trips, Amtrak is a really underrated option. I travel semi-often from Pittsburgh to NYC (450 mi) and choose train over flights because it's actually not that much slower (consider to/from airport, security, and (de)boarding, as you say) and it's much more comfortable: I can walk up and down the whole train, with no fasten-seatbelt sign to stop me; there's a cafe car; I have about 2 feet of legroom; there is reliable AC power and functional wifi. I just make it a work-from-train day and all's well.