We love Less CSS, and we’re trying to get the Drupal integration of it to work as part of an automated site build/install using Drush. We’ve opened a ticket to try and figure it out.
It’s a great acid test for a module, to try to build a site with it, without doing any fiddling that can’t be done with drush make/drush site-install. It shows where your module’s “expectations” might in some cases be “unreasonable”: it’s like a UX test, but on drush’s behalf rather than a human beings; “can drush use this module?”