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Just in response to your last point about webmail not catching spam, Gmail does a great job and has let through about two spam messages over the entire duration of my use, which is about two years. So it's not a "free service" problem, it's a "lazy free service" problem. Read: Microsoft Hotmail.
http://www.419eater.com/
@Carl: That's the one I've seen. I like the pictures they get spammers to take, esp. the one with the loaf of bread on his head.
And as for spam, my Hotmail account was set up as my spam account (you know, I have to give an email address on a website but I really don't want to kind of thing). Recently, the amount of spam I receive went from something like 30 spams a day to 0.5. Not sure what happened, but that was a huge improvement. Now only my Yahoo! account gives me major spam.
The other thing I haven't figured out is how do I get spam IMs? (only happens on my Yahoo)
@ChrisRowell: I can't speak for my dad, but my mom is pretty suspicious of anything she gets that doesn't have a name she knows attached to it. She even catches stuff that purports to be from herself. Phishing and spam are both lost on the two of us. My dad has a spam filter in Outlook, but I don't know if he ever reads the messages or if any make it to his Inbox. (The rest of us use webmail services; he's the holdout for desktop applications.)
GMail does a good job trapping spam, but as you say, somehow spam finds that account. I didn't give it to services before 2006, but I still got spam. It's just nicely hidden away in the spam folder.
Yahoo got better, but has backslid recently. No idea why. It's impossible to compare to my work account b/c the policies are different, i.e. the trapped emails rarely make it to me for review.