This has been discussed here before. The solution is less than ideal, but an upcoming version of Android (I believe 2.2 will have it) will allow for the core OS and the apps to be separated, and the apps can be updated independently. This means users will get the latest version of GMail and Calendar the same way you get Maps now, from the Market.
This way at least the users will get most of the front-facing feature upgrades.
They can do that now though. I know you can update the Google Maps application from the market.
It doesn't really help much with the core OS though. You need Android 2.0 to support more than 256MB of memory in a device. Same for multitouch and a whole bunch of other core OS libraries. There are apps on the market that require specific versions of the OS and don't even appear if you're running an older version. Several handsets have been discontinued in terms of software support and they're now forever stuck at 1.5 or 1.6 if you want official firmware. If your device doesn't have a known exploit to root it then you won't even be able to use third party firmware.
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