I heard about SASS (http://sass-lang.com/) not long ago, and had an opportunity to use it in the recent uPortal Mobile work. In my opinion, SASS is CSS Awesome. It is everything that CSS development should be, and makes CSS truly programmatic with things like variables, mixins, loops, and functions. I will be using SASS for all my future CSS development. I'd like to recommend using SASS for uPortal CSS development.
Impacts to uPortal:
For front-end developers, an uptake of SASS. Source code "CSS" would be done in SASS. SASS exports to pure CSS, which would be the uPortal skins. SASS runs on Ruby. CSS development and maintenance becomes *much* easier.
For portal adopters, the impact is probably nothing. Adopters would be working with the resultant CSS file (and likely never interface with SASS), and any customizations to a skin would be done in the same manner as before.
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