Well, that depends on where and which airline you're using.
I've used AA several times and haven't had any problems. The gate agents have even gone so far as giving more than 1 pilot a ride in the back on an MD-80. I believe their rule is still 1 ride for each jumpseat in the cockpit. So I was pleased about that.
There are numerous threads on this site about jumpseating and which company policies are in existence. That might help for additional information.
With the holidays and additional flying that is to be cut by AA, I'll have to rethink my commuting in/out of STL now.
If you can be flexible enough to go in/out of LGA as well as JFK, you've just increased your chances. But that's obvious I suppose.
If you have specific questions, just give me a PM.
My pilot commutes each week from ATL, he was commuting from DTW but we moved. It isn't too bad most of the time. He usually gets on non-stops and DL pilots are pretty nice about writing themselves a pass if they see another jumpseater from a different airline but we have devised a back up plan through connecting cities for holidays and busy times. It has been working for 2 years. It helps to have a travel agent for a partner though. He is always calling me from the airport asking me where to go when flights are full.
I don't have personal knowledge, but there was a guy interviewing with me at ATA that worked for Jet Blue and lived near Chicago. He said commuting to JFK was a nightmare and was likely to cost him his marriage if something didn't change soon. Hence, his interview at ATA. Unfortunately he didn't get hired at ATA so he's still dealing with the commuting I guess. I hope things are going okay for him because he seemed like a really great guy. Guess his wife should be happy that he has a job in this environment.
I believe I know who your man is. He's praying he finally gets a line for Sept. isn't he?
Did this guy fly for Kitty Hawk before? If he did, he's on at South West now, so don't cry too hard for him. He was in initial with JeffG and myself and you are right. He is a great guy. His commute problems were happening right after 9-11 when we didn't have American or Untied back yet for jump seatting.
Not sure where he was before but if he got on with SWA I'm happy for him. I guess I'll email him and see how things are going. The thing about this whole deal is you really need to try to see the best in whereever you're at right now because it's just not worth being unhappy all the time. If that happens to me I'm going to go fishing and make my wife work harder.