I recently stumbled across a project that has 27 different CSS files used by the same theme, and they are for specific sections in the application, rules split like this: there's a CSS file for the menubar, there's two more files for contact forms, another one does the footer, specific-page formatting, two more for galleries, so on.
So I asked lead what's the reasoning for so many CSS files and if it's safe to concatenate.
His reply was that all files sum 126KB, bandwidth matters and there's 500+ CSS rules, so best not concatenate to prevent selector collisions.
I know that 126KB of uncompressed CSS files is an awful lot, but I also know (from the best practices guide) that all these files should be downloaded single shot, so browsers will cache one biggie instead of downloading them one by one across the browsing session.
Why should I not keep myself from gluing all these files together? Is it a big deal?