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To me, Microsoft keeps churning out the worst looking Desktop OS (that's a subjective opinion, you don't have to agree with me) with underlying systems presented by professional failures. Just the other day I spent hours trying to fix a problem on a Windows 7 machine, making no progress, and...

Security? Microsoft? ... What?

It's interesting that you brought that up. Every version of IE for the Mac did something significantly differently to its Windows counterpart that actually made it more difficult to design a site that even worked consisitently across what was on the face of things the same browser...

IE is useless for the simple reason that it is not, nor even has been, cross platform. Because even when they try to do standards compliance, Microsoft seems to have an odd definition of what is standard behaviour, it has become a thorn in any web developer's side. Hopefully IE9 will fix that.