Google "CSS".
And digest first that it's the order of CSS code which matters - hence, the order in which the same code is in one single file, or the order in which CSS files are loaded if the same code is spread out across multiple files. You can have 10 different body backgrounds across 5 files, but the last one wins - unless there's a single "!important" in between.
Which is why many - wise - template makers, or smart site designers, make sure that a particular file, often the so-called custom a.k.a. override CSS file is loaded last. In that you can pretty much do what you want, then. You'll (almost) always win - exceptions were mentioned above. So, who cares what extension developers do in terms of CSS, and where they store their files. Sometimes it's better to "unload" those files anyway, as it gets too often in the way of a neat template design.
So, then it's almost only a matter of how much or less bloated you want your code, IOW how many more or fewer bytes you want to have the user loading before the pixels show up on the screen. Which sure matters more in some parts of the world and/or data "highways" more than in others. It's probably equally important to avoid chaos and have things kinda "together". In the age of Firebug & Co it seems maybe less important, but IMHO strategy is a wonderful thing - but what's new.