Only risk of the C1 cached css-files is that you would potentially have to browse the whole site through to make sure you have hit every combination of templates and functions :)
By running a tool like Grunt or Web Essentials you basically just point it to the folder with less files and it spits out all the possible css files.
Its a sensitive subject and reading through blogs and tutorials it really doesn't look like most people use a workflow where the server processes less/sass files. Its usually done as a part of the development cycle directly by whatever editor you're using, ie. in Sublime, VS, Crunch, WInLess, less.app, CodeKit, Notepad++. The options are many.
By running a tool like Grunt or Web Essentials you basically just point it to the folder with less files and it spits out all the possible css files.
Its a sensitive subject and reading through blogs and tutorials it really doesn't look like most people use a workflow where the server processes less/sass files. Its usually done as a part of the development cycle directly by whatever editor you're using, ie. in Sublime, VS, Crunch, WInLess, less.app, CodeKit, Notepad++. The options are many.