[mceachen]

I couldn't get my Dad off Windows, even though he kept getting malware and viruses and ask his helpdesk (me) to repair the damage (which meant hours of formatting and reinstalling windows and N apps and ...). Inertia and "but this is the way I do it" are hard to fight.

FWIW, if you're running Google Apps for your family email, you can require a certain level of password quality, and force-reset the offending passwords.