One thing puzzles me: If LESS is essentially a template language specialized for CSS, why not reuse the template engine that you use in your application anyway? That way, you'd also have the benefit of defining often-used attribute values (e.g. colors) in a variable, and you could also group often-used combinations of attributes together in a variable or sub template.
I'm seriously considering writing a Python-based "Preprocessor" language which lets me drop in Python code on any file, and deals with transforming it into the final "compiled" file.