Help creating a smart playlist - all video from one group and fill to size

I have two classifications of videos:
A) current videos added randomly to iTunes
B) old videos I'm trying to work through in chronological order but are less important than 'A'
I have a 8GB Touch so space is limited. I always have 2500 MB available for videos.
It was easy enough to separate the two classes of videos into two smart playlists, A and B.
Now I need your help to create a third Smart playlist that contains everything from A , then fills whatever is left of the 2500 MB with videos from B.
Or, if playlists aren't an option, do you have any other ideas?
Thanks

The new tools in iTunes 9 made this possible, at least good enough.

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