I'm not sure I'd agree 100% with StarTekh. I'd say this:
If you're system is running stable, and there's nothing wrong with it, then you'd ideally want to avoid messing with it. If you do, be prepared to kick yourself in the behind and rollback the updates.
If it's a net-PC (which I assume most DAWs are at this point), then Windows, Java, Adobe, etc. updates are a necessary evil (just for security purposes), but I'd avoid driver updates like the plague on a stable system.
Now...if you're system is NOT stable and you suspect one or more drivers are giving you issues (like a bad video driver causing crashes when watching videos), then you could always try to upgrade one at a time versus all at once. This way, you can give the update a few days to see if it addresses your problem or not before updating the driver for your next system component.
With all that said: I personally try to keep things up to date, but then again, I've never had that fabled "entirely stable" system.