can we hope to see this on the DreamPlug
a way forward from Jaunty
That is entirely up to you guys, it is not that difficult (once a distro has been built, that's the hard bit).
You have a few weeks reading time before the distro's are going to be ready for ARM, so why don't you go visit the Ubuntu faq/forums and find out how it's done.
design and implementation is waaay over my head
You don't have to design anything, and I would hardly call typing 'debootstrap' or 'apt-get upgrade' heavy implementation.
You have access to a great OS, isn't it time for you to learn a little about it

Oh, and if you really don't want to learn how to do it yourself, you can always pay someone to do it for you (just as if you were using windows).