Did you ever check out JFarrow's tip about a CSS cruncher? I haven't tried it, but it might be worth a shot.
I have, don't recall why I didn't adopt it then.
Does it work? I've never tried it.
I guess it depends on what gets stripped off and modified
There are trade-offs. Heavy CSS compression can make it unreadable and difficult to maintain.
Cross-browser compatibility may suffer when symbols get combined or reordered.
FYI: JenSocial has a great tip for this in her VIP group. I use it on two of my networks and have had no problem with it. It has allowed me to add a ton more css code.