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If a user isn't educated enough to know how to open up a port he needs to run a particular program that needs a hole punched in the firewall, then that user shouldn't have unfettered access to the Net anyway.
I don't agree that switching friends and family to Linux or Mac OS X will solve the issue of providing free tech support though. Not only would you have to train everyone through the learning curve, but those OS's still need to be patched and updated as well. Hell- I used to support a company with about 30 graphic designers using Mac's and even though the PC's outnumbered the Mac's 5 to 1 I spent half of my time answering help desk calls from the Mac people.