Trouble with that idea is that to a certain extent generalizations and stereotypes apply. Not in every case, certainly, perhaps not even in the majority of cases, but it does apply just enough to keep the stereotypes alive.
Yep. I look at people's behavior a lot like a drop of water running down a window. Each individual is like a molecule, it's completely impossible to determine that individual's path. It acts according to the rules of brownian motion. It could evaperate, zoom around, sit their, soak into the glass, whatever.
But when you get a few hundred million or so molecules in a single mass, say in a single drop of rain, then you can predict their movement pretty accurately.
Security will be a issue for linux users. To a certian extent it already is, older Redhat distros did the same mistakes that MS did with w2k., which is make it default to install everything under the sun. You had ftp servers, telnet, http servers etc etc etc. So anybody tooling around with those distros that haven't bother to upgrade are practicly script kiddie playgrounds. In windows you have to be carefull, because as a cracker you don't have a clue how the system will react. Windows has a lot of black magic mojo (from the perspective of a attacker) going on so it's easy as your doing your cracking to crash and generally screw up a windows install. But in Redhat 7.2 it's easy to understand what is going on and know what not to do to attract attention.
That's why good package managers are critical. Continously upgrading is something that people realy need to do, and sticking the update in a cron job will be easy to set up for even my Mom.
Moving away from numbered releases and big sweeping upgrade cycles imbetween long periods of stagnetation is not cool. The Debian model of "stable", "testing" and "unstable" is realy cool and plays off of the strengths of linux in a major way.