Would it make a difference in ride quality if i were to upgrade my stock loose ball headset to an orbit X? Or would just some maintenance and grade 25 bearings be about the same?

Edit: How often should I re grease the loose ball headset if I keep it?

Unless I'm dealing with a horribly pitted, crappy caged bearing headset, I honestly can't tell the difference. I've never gotten on my bike and thought, "Upgrading my bearings would make this thing turn so much more smoothly."

How often your headset requires maintenance depends on a lot of variables.
..

I can not help but feel like that was directed at me.

Yours was the one I was thinking of! That was the worst one I've seen in a while.

thanks.

Tires would change your ride quality way more for similar money to a good headset.

I bought some gp 4000s they are awsome!