Alternatively any software for
redacting the css to reduce repition
and size?
Yet another level of indirection ... You (and your team) should write long CSS files with as many comments as needed and then write a tool that will publish merged files as needed (different templates need different files), stripped comments and minified as http://www.cleancss.com could do (CSSTidy). Readability comes first if you wan't to be able to modify a file in 1 month or keep track of modifications (or worse if sb else must do that!).
Other options are to reduce the number of templates used throughout the site. No need of two templates with 2px differences (grid layouts are a good way to stick to this) or inconsistent ways of displaying error messages. Define a common look and feel to your site and give instructions to webdesigners, if it isn't already done.