Trying to create a Smart Rule for an Personal Section that will show for a specific genre OR label as shown below - doesn't seem to work? Is there an ability to do an "OR" (even in the Advanced Editor)?
Smart rules are AND'd together.
You could use the batch editor in DVR > Manage to find all your movies with the genre Holiday, and add the Christmas label to them at one time. But of course, you'll need to do this to any new movies. But at least it's a head start.
If only we could get a Label maker in passes that would apply the Labels we specify to its recordings...