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I'm asking this question purely from an ease-of-development standpoint.

Performance is not a consideration, because we will have a build process that combines and compresses all our CSS files into a single file for release and then compresses it.

But which will be easier for a team of front-end developers to work with? Multiple files or a single file that is separated into distinct sections through comments?

+4  A: 

If you're going to join and compress all the files at a later stage - I would most certainly split them into multiple files and organise them accordingly.

Check out how jQuery UI organise their CSS files, they have about 7 CSS files, and 1 main file which imports all 7 using the @import statement. This might be useful to you so you don't have to have 7 <link rel="stylesheet" /> references.

Also make sure you order them accordingly so that any overrides are always at the bottom.

Good luck

Marko

Marko
Thanks Marco. I'll have a look at the jQuery files and how they're organized; they sound like a good setup to follow.
jonathanconway
Your welcome - I found the files in my custom UI package in the folder development-bundle -> themes -> no-theme
Marko
but @import is not advisable for performance http://developer.yahoo.com/performance/rules.html#csslink
metal-gear-solid
"If you're going to join and compress all the files at a later stage...."
Marko