Going from 12 Years on the Mac to a Windows XP Notebook

You need Tetrinet. Just letting you know.

If you actually have an iPod stick with iTunes, but only for syncing. Use something else for playback, because iTunes is a memory hog. I prefer Winamp to VLC on Windows simply because Winamp has a persistent local library, meaning I can pick and choose what to play more easily. Plus, Winamp's visualizations are great - Milkdrop specifically - better than anything I have seen anywhere else. As a bonus, you can copy your entire Music folder directly into My Music, fire up iTunes, and after a long wait while it rebuilds your library, all your media is there, indexed and ready to go. No conversion necessary. The only thing that might disappear are any album art you let iTunes download for you - for some reason that doesn't sync between machines well. Also remember that on Windows, overwriting a folder doesn't work like it does on a Mac: Only file names that match are replaced, others are left untouched, including nested files and folders. On a Mac, overwriting is like deleting the existing folder (and all subfolders) and completely replacing it with the new one. It's a bigger deal for those going from Windows to Mac, but worth mentioning nonetheless.

http://www.microsoft.com/Security_Essentials/ for anti-virus -- free! and works ok!

I had to make the same switch after 20 years of using Macs. The only thing I found superior on XP was MediaMonkey. The rest was either (to me) essentially equivalent or just a bummer. I still have to use XP at work, but have used Linux at home for the last four years on a homemade PC and now on a netbook. It beats XP hands down in the same ways OSX does (ease of use, security, speed, lack of crashing, innovation) and there is a lot of impressive software available which is getting better and growing in number every day. As a fellow former Mac user, I'd really urge you to take the time to check it out.

iTunes for Windows is the shittiest piece of software ever written. As mentioned above, Mediamonkey is several orders of magnitude better. I just had to repeat this for emphasis. I split my time between Textpad and Vim as far as text editors go. Both are great.

Second the use of Launchy for a Quicksilver replacement, I couldn't live without it when I used XP. Openoffice is also fine on Windows now, and much faster than it used to be to start up. Second also the recommendations for mediamonkey. It's excellent at managing large collections and will I think sync with an ipod. Autohotkey is free and the nearest there will ever be to applescript on a windows machine. I use it for title-casing and similar little scripts all the time.

You could also install Liberkey instead of 50 separate applications. It's a collection of portable apps with combined updating and even file associations. No further installs necessary, no slowing down the OS. "Liberkey Ultimate" covers at least 90% of your list. No harm in trying. You can still install iTunes if you don't like the portable alternative, you don't even have to uninstall anything. *Bonus* if you install Liberkey in your dropbox folder, all your applications are available on any windows machine with dropbox. No more installing apps, utilities, media players, browsers ever again.

OpenOffice roxors. Google docs? I found viewing a simple file in that difficult; I can barely imagine using it to write a letter, let alone seriously word process. And I couldn't live without my OpenOffice Calc (spreadsheets). That's the only budgetting/money program I need. I have MS Office with Access for my occasional relational database needs, but I preferentially use OpenOffice for everything else because its interface is so nice (especially Calc). I even use OO to translate Word7 docs for colleagues who only have MS Office 2000. OpenOffice is the finest free product on the planet. Except for air -- I really like air. But OO is right up there.

WCityMike, if you burn your iTunes Store purchases to CD, then re-rip them back into iTunes (or whatever media player) as MP3s, they'll be plain old MP3s from then on, no DRM attached.