Matt, you make captain? Congrats! Even though I'm not over there anymore, I'm pullin for you guys! I've sat in SWA's second jumpseat before, it's not THAT bad.
I think SAT is has our largest population of commuters of all our cities. Most go to HOU or DAL, but there are a fair number who fly out of MDW as well.
For what its worth, I commute on SWA every week(MDW-STL) and they are by FAR the single best airline to commute on. Good availability and very friendly to off-line commuters.. in the last 6 months I've only not made my first choice flight once.
The comfort of the second jumpseat depends completely on your height and the captains height. I'm 5'7" and I rode it once with a captain my height.. very comfortable, I've also done it with a 6'4" captain, and the 37 minutes to STL were painful.
While the logbook location on your 73's makes for some intimate reaches, nothing tops jumping on an MD-80 where the cabin phone is literally under the jumpseat and they have to reach between your legs to get it. Especially if there is a female pilot involved..
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