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As far as I am aware, saved files need a game to boot them up. So if you had a 10 MB mini game sitting on your HDD, I don't think it would be possible to run this as a game, without using a boot CD. That's just the way the dashboard currently is. Unless M$ have thought about this and made it possible to run certain types of files straight from the dashboard (like the ripped CDs). But I haven't seen anything about this so far, so it's probably impossibe.
As for VCDs, this would also need a big upgrade. I know it's possible to do this using the HDD, but I don't think M$ want to get back into the reputation of releasing a load of patches to do these things. It could just ruin their console reputation.
Maybe we could look out for it on Xbox 2?