Yes, on many occasions. But it has always been ruled out as an option; usually, as you alluded to, with administration being cited as at least one of the leading reasons for why.
Note also that Air doesn't quite care if others are doing X, as they don't inherently worry about following the pack. Often because it turns out they're ahead of the pack anyway, as many competitors only do things for reasons related to marketing and not because that thing will necessarily increase security or privacy in real terms. So for example, many a competitor may say they accept Bitcoin and say no more. While Air recently cut out the middleman for Bitcoin transactions and remains one of the few, if only, to do so I think. When this sort of thing is taken into account, you may see how sending cash physically may seem wholly unnecessary from Airs standpoint, besides just unfeasible practically .
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