Airlines just aren't that organized.

My travel agent (for when other people are paying) and my Expedia prefs (for when i'm paying) hold most of this stuff, but i still call and go over my preferences with a live person. Say what you will about CO service, i have had multiple thoughtful employees get small details right as a result.

But the fact that they have to manually override it every time means that a)they're intentionally not trying (yeah, right) or b)they just don't hold this info. I go for the latter.