Hi, late to the game. Just got back from a cruise.
Personally, I have a weirder suggestion.
Try: Ubuntu 9.04 and slowly move up through the distros as you begin to learn how they work. See how shit borks and whatnot throughout. Learn to use the cube, then hit the newer distros and be prepared to be confused as fuck for the new almost tablet style distro.
Then go fuck around with mint, archlinux, fedora or whatever.
Why? Where is the merit in this quest? Then you'll have a user who gets frustrated because, in all likelihood, there will be at least some things that they have to learn how to do two or three times as methods change and old practices become obsolete. You're also recommending that users run outdated software, in a version of the distro that won't be supported (at least not without complaints) in their forums or IRC help channels. And Ubuntu is the only distro I've seen that's hopped on to this stupid, "Everything must be a tablet, oh god, I'm so ashamed to admit I once used something called a desktop!" bandwagon. I haven't any other distros that have changed over to a tablet-style UI by default for desktops.
So, basically, your recommendation is, "Go use old software that's probably not maintained and may have security issues or bugs that won't be solved. Slowly move up to a current install, and then get ready to have an initially unuseable GUI. Finally, after you've done all this, abandon Ubuntu and move on to something that does things completely differently." In my opinion, taking this advice is a recipe for making yourself hate linux. I'd still recommend people do a little bit of research, and find a disto that looks like it meets their needs. Play around with liveCDs or bootable thumbdrives for experimentation purposes. When you find one that clicks, stay with it for a while. Having a consistent way of doing things in a distro for a year or two can go a long way to keep you from getting too frustrated. I'd be interested to hear why you think this is a good idea, but as it stands, I see no practical gains from doing this, and the potential for the user to just get frustrated with things and give up. Perhaps if these were IT professionals who might have to maintain a server in a corporate environment that takes ages to update, because theydon't want to have to redo all their in-house scripts and tricks when something changes, this might make sense. However, it seems like these are just general users who thought it might be cool or useful to know a little bit about linux. I wouldn't tell someone to install Win98, and then move up to Win7 over time, and likewise I can't see recommending doing this for linux.