Hi Cassiel,
If it’s at all relevant, I’m running my main layout CSS through the API, rather than using real files. It’s allowed me to split the CSS into several files (for fonts, layout, furniture and so on) but only have one http call. It also makes use of MODx’s caching.
I created a series of chunks to hold the actual CSS rules, then a document in the file tree (CSS file type) to call them all.
So far as I know, most regClientCss calls are optional, so you could easily include the relevant CSS in the main CSS file.
You can also remove extra http calls for IE-specific CSS files by using a conditional comments div per
http://modxcms.com/forums/index.php/topic,16377.0.html.
I’m afraid I can’t help on the compression front