This is why rail works in the DC/Baltimore/Philly/NYC/Boston corridor. Regional rail is perfectly reasonable. I don't expect to see NY to LA anytime soon.

Aside from regional intercity rail, however, there still exists the problem of what to do once one gets there. I live in metro-NYC and frequently work in metro-DC, but I drive. I can get to Penn Station in NY very easily, and then get to Union Station in DC, but I can't get from Union Station to Northern Virginia beyond the beltway easily at all. Rail doesn't help me until I can get from Union Station to Herndon or Reston efficiently. In all these areas that developed after 1950 or so, the business destinations were spread out on the periphery - probably to avoid the taxes of the cities. It is really difficult to serve an area like Houston with subways/buses/light rail.

You are correct to a point. The Windows OS family has had a lot of attack vectors that don't require user intervention - worms and such - as well as many many vulnerabilities in tools like the default browser and email client. Mac and Linux systems have had far fewer of these vulnerabilities. A reasonably hardened XP system with the firewall turned on, various services turned off, and using Mozilla products instead of IE and Outlook Express is reasonably secure.