Paint me suspicious (but if you do, please use water-soluble paint as my wife hates that colour on me), but it feels like you're almost asking someone to convince you to go to Linux. If so, please post your question on /.. They're good at blind linux advocacy.

That said, as someone who has avoided Windows like the plague for about 10 years with reasonable amounts of success (and attempts going back another 3 or 4 years prior to that with less success), I'll shut up now.

Well, mostly. I will say that you may want to figure out what you want to focus on - web, perl, or OS - and keep all other things constant. If you don't want to learn Linux, don't. Use Windows. If you don't want to learn .NET, don't. Use Perl. If you're willing and/or interested in trying other things, go ahead. Linux is free anyway, so it's only a commitment of time, not money, to try it. But don't do so because I tell you to do so, do so because you want to spend your time learning Linux. I did, and I like it. But you're not me, much to the world's happiness, and you may not be interested or may not like it, or may not have time. Those are all valid reasons to focus elsewhere.