Don’t go crazy
You can indeed break your css into manageable chunks of code (you couldn’t use a better word, since what I am going to point you toward explains how to use MODx chunks in your CSS). Some call it modular css, I call it plain common sense and a MODx blessing : native server side css capabilities make this child play. Yes, MODx is not limited to a text/html document type which is real cool.
Just read [Tutorial] Use CSS as MODx document
With this technique, you won’t need multiple css files, but multiple chunks which you’ll insert in your CSS document. You can of course enjoy the same benefits you enjoy in your html templates, that is content re-use (sure makes our life easier

). Why is that ? Because your CSS document is dynamic and parsed by MODx. You can have chunks in there, but possibly snippets too (though right now, I didn’t try it, but I guess you could implement a random background pretty easily for instance...). One thing : TVs won’t work, don’t ask me why, Susan found that out I don’t remember the thread... I think it has to do with the parsing order. If I find it I’ll update my post here.
Now about js, I have never tried this with Javascript, but I suppose it’s theoretically possible (here is an interresting thought...).
As for the need to adapt your CSS or js according to which page you’re on, that’s also possible but it will involve having multiple templates. Unless... wait a minute, I just got an idea ! I’ve never tested this but it would be an interresting thing to try out : download the
OutputIfPage snippet and use it to modulate your CSS call according to which page you’re on (Man, I am gonna test this tomorrow that would lower the number of necessary templates

)