I appreciate all the thoughtful responses!
Interesting to know about the 'underground' market. Hmm!
And also reassuring, somehow, that others have messed up even worse than I did here (thanks NYCommuter ).

What still bums me out is (at risk of sounding a bit too entitled) that my status w/ AA is meaningless. Or that they, frankly, lack a sense of 'going above and beyond'. Let me give some examples of companies that get it:

• When my mom was (genuinely) sick, Southwest Airlines graciously extended her expiring credit without a fuss.
• When I forgot I had an expiring $100 voucher with a local Mens Wearhouse, they agreed to extend it by 3 months at no charge.
• When I found a big price difference between what I paid for an item 3 weeks ago vs. what I saw it for that day, Amazon kindly offered to credit my account for the difference in full.

But, other than Southwest, airlines seem to have a "no exceptions" policy, goodwill be damned. For example, I was working with teammates in Beijing and had made many one week SFO-PEK trips in the past with United. One time, I messed up due to getting confused by their date picker and booked a trip for 5 weeks instead of 1. Two days after booking, I called to ask for a courtesy change (and it was months in advance of the flight); they said, nope, $250 change fee.

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Increasingly, I think if I could fly Southwest (or Amazon Air) for all my travels, I'd do that. Goodwill should be two-sided. If I recounted the vast number of times planes got me to my destination late, temporarily lost my luggage, etc... you'd think they'd be a bit more humble and forgiving, right?

Gah. Okay, thanks for letting me rant there. I feel a bit better now.

(and yes, this is a bit pathetic, given that I'm a very experienced traveler; I know better than to let certs expire, and I darn well know that most airlines are sticklers for the rules. Just had an irrational hope... )