Trying to be OS neutral (kind of hard as I am a Linux evangelist of sorts) I'd have to say there is no (well, not true, there is some) shame in using Windows if you are happy with it and it totally fills your needs, be they social networking, email, Office apps, gaming, whatever. If, on the other hand you also hate getting viruses or the threat of viruses, shelling out $30-$60 per year for antivirus software, buying a machine WAY more powerful than your needs dictate simply because the anti virus software consumes all available CPU and disk then Linux is a completely viable alternative. Now, the Linux you are using at school, is it a graphical version or a server version? I ask because it shouldn't feel foreign. LibreOffice is just about a 1 for 1 drop in replacement for Microsoft Office (Word, Excel, Powerpoint) (Write, Calc, Impress). F1 is help, etc. The thing of it is, you should not feel you have to fight with it or, otherwise, have to 'get with the program'. If Ubuntu feels awkward, try Fedora or Mint.
I actually do have iTunes on my XP VM. I seriously do not like Windows. I consider XP to be the first, perhaps only, properly working version Microsoft came out with. What I did when I was working at Monster is I had Linux as my main dev environment but as Evolution mailer never quite worked right with Microsoft Exchange, especially for meeting notifications, I dropped in VMWare Workstation and brought that up on its own monitor strickly to run Outlook. Here I have VMWare Workstation only to support those apps that can't run on Linux and, thankfully, there aren't that many I need. If I were a gamer, I'd so be doing Steam and paying them to continue supporting Linux as a platform. (Thank you Nixie!)
Trying to be OS neutral (kind of hard as I am a Linux evangelist of sorts) I'd have to say there is no (well, not true, there is some) shame in using Windows if you are happy with it and it totally fills your needs, be they social networking, email, Office apps, gaming, whatever. If, on the other hand you also hate getting viruses or the threat of viruses, shelling out $30-$60 per year for antivirus software, buying a machine WAY more powerful than your needs dictate simply because the anti virus software consumes all available CPU and disk then Linux is a completely viable alternative. Now, the Linux you are using at school, is it a graphical version or a server version? I ask because it shouldn't feel foreign. LibreOffice is just about a 1 for 1 drop in replacement for Microsoft Office (Word, Excel, Powerpoint) (Write, Calc, Impress). F1 is help, etc. The thing of it is, you should not feel you have to fight with it or, otherwise, have to 'get with the program'. If Ubuntu feels awkward, try Fedora or Mint.