"He was expecting a 'windows' sort of experience where you just bung the disc in, install then go for all the updates."
Except that's not the WIndows experience. It amounts to running the install CD. Then go find your drivers. Then update, reboot, update, reboot, update, reboot. Then go find an app, download, install it, find the next app, download, install it, ad nauseum. Then a week or two later have like 5 different updaters reminding that updates are due for those apps that were installed.
MOST of the people I talk to who are afraid to go off Windows, go striaght to a tirade about how unreliable and problematic computers are. They list their specific grievances, and I then point out "Those are not *computer* problems, those are Windows problems. If you ran Ubuntu, or a Mac, or whatever, none of those problems would occur." (Or, if they *did* come up with legit computer problems, "none of those problems would occur except a and b".) It's strange, to me it's like if almost everyone drove Yugos, and were like "No, I love my Yugo and won't switch. It's to bad cars all have doors that fall off, handles that break, need carburetor adjustments, cap, rotor, and plugs pretty frequently, don't want to start sometimes, and generally break down so much."
Back on topic, Canonical etc. are making the right move. As a few commenters have said, the first time someone goes to a flash or a java page, it's like "you need to install Flash (or java). Click next to do that." And then it does. Some people feel strongly about not wanting flash on there, and the rest it's a few click install (or checking that box) anyway.