One thing that I had a problem with when converting non-tech interested people to linux was the unavailability of apps like google talk and yahoo messenger. I think empathy can do voice chat on google now, but yahoo is still off the table( which is a problem, because most of the people who you're talking about probably still have yahoo ids). As for the distro, don't choose anything that doesn't have synaptic or some other package manager where it is EASY to enable non-free repositories. This is absolutely critical, and the main reason why fedora failed totally with my friends when I tried to get them to use it. As for look and fell, most people just ignore the interface altogether and distill what they want pretty easily, so don't worry about that.

Seriously, why the hell does Firefox struggle so much with slashdot? Chrome seems to do it fine.

Can somebody show this to Nicholas Negroponte? Put sugar on this and you have your OLPC laptop.