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I don't know anything about how heavily you've modified Windows, but I just switched to OS X from Win7 a month ago. This is after only ever using Windows. I was surprised by how easily I made the switch. I know Lion gets mixed reviews from long time Mac users, but I'm a huge fan.

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Well, I have autohotkey modifications which give me a vim-like keyboard everywhere, add all sorts of shortcuts to switch to my most-used windows (browser, editor, etc.). Plus I have programs for everything I need to do, etc.

Honestly, the two biggest problems I have with switching are my AutoHotKey customizations, and Total Commander, which afaik doesn't exist for OSX.

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