500 mile upgrades are going to be a bit weird for the next couple months. The reason they’re no longer refundable is because the certs are going away, and they’ve offered options for converting previously paid certificates into loyalty points, miles, and other options. And they want to offer that flexibility to people who bought them over the years without enabling people to buy a whole bunch now to abuse the conversion options. Ideally I’d agree an exception could be made for situations like this where you bought certs because of a confirmed upgrade which later came undone, but for now the terms are black and white that purchased upgrade certificates are non-refundable. It’s literally bullet #1 in the 500 mile T&C’s. (
https://www.aa.com/i18n/aadvantage-p...p#terms500mile ) Caveat emptor.
Regarding this part:
Total time spent Saturday on AA's failed flight debacle -- 4 hours
Total time spent Sunday actually travelling -- 8 hours
Total time spent Monday soliciting AA service recovery consideration (mileage, refunds, vouchers) -- 2 hours and counting.
I don’t understand why you even listed travel time. A cracked windscreen is not exactly preventable… while it’s unfortunate you were delayed, cancellations are a part of air travel and AA issued you compensation. Why you choose to invest so much effort negotiating/chasing additional compensation for a routine cancellation comes down to a choice. Contractually AA has no obligation to you other than to either fly you or refund your ticket, and in the case of overnight cancellations within their control, get you a hotel. AA does proactively initiate compensation for the more severe foul-ups, but for a routine delay or cancellation, fire off a succinct email in 5 minutes and call it a day.