Originally Posted by ShyTorque
Your second wish is already granted. Garmin 530/430 series databases are upgraded exactly like that, via a removable card and a PC adapter (and a subscription package).

Ah, that's quite cool! I was thinking more of over-the-air updates, though. I believe the high end Garmins can do current weather info live, so why not firmware updates that way too? For comparison, my phone can upgrade itself from anywhere* without needing me to plug or unplug anything, and I don't need a computer either. The latest digital radios can do this too, via a (usually wifi) connection to the internet.
* anywhere I have a decent 3G signal, that is.