It would be nice to have something like $REQUESTpath? =~ "/var/www/customer/subdir/" { ... }
I don't know if this is even possible, but while developing a patch for SysCP (control panel like Confixx) a problems arose: A lot of the settings should be directory-specific, for example authentication, error pages, ... and currently it's not possible to do such things with lighttpd. For now I hacked up a combination of $HTTPhost? and $HTTPurl? but this gets very messy (think of x1.example.org => /var/www/, x2.example.org => /var/www/foo and you want to protect /var/www/foo...).
I already thought about doing this with a mod_magnet script as you can check against the physical path there, but things like password authentication etc. are not possible there (at least not as easy as with the config file).
SysCP of course is just an example, such a conditional can be useful for any other "automated" config generation system as well.