I'm going to assume that this machine is totally for work and ignore stuff like games and whatnot.

VMWare: I've run a lot of Windows as VMWare under Linux, mostly 98 and 2k, IIRC. I've run them both at the same time and they still work marvelously. I've never had many (if any) issues with the copy and paste, as it just seems to work after you install the VMWare drivers in the guest OS, and they don't really suck up that many resources; just make sure you've got a good amount of memory.

Macintosh: MacOS X does not have a built-in X server. There are third party ones available, but they're likely to be as flaky as XWin32, though you would have compiling support. Even though MS Office is available for MacOS and MacOS X, I still try to avoid them. Even so, I got the demo version of Office v.X just to see and it seems very nice. But it still costs about $450 when I can get AppleWorks, for example, for $80 (not that I've used it).

I don't know anything about Outlook's todo lists, honestly. But you might want to take a look at Evolution for Linux. It seems to work pretty well for that sort of stuff. Office v.X has ``Entourage'', which seems to be a step beyond Outlook.

jEmplode works very well, not quite as rock solid as emplode, but close enough. Under Linux, I don't believe there's any drag and drop support, though. There are a number of mp3 tag editors for Unix, some nice, some not so. I'm trying to come up with one particularly nice one now, but I'm drawing a blank on its name for some reason.

I personally don't like iTunes. By default, it keeps everything in what we call a soup mode, and it doesn't understand articles, so ``The Who'' is under the `T's. You can create playlists, but you have to do it manually. No drag and drop, AFAICS, as that just puts the files in the soup mode. You also can't just play a tune without it adding it to its soup, which is especially annoying for clips from CDNow, for example. I do like the fact that it doesn't support skins, but that's just my asinine prejudice.

There are a couple of financial apps for Linux, which might work fine for you, depending on exactly what you do with Quicken. GnuCash and Moneydance are the ones that comes to mind.

You can still purchase a multi-button mouse for your Mac. And Apple laptops, while heavy, are remarkable. None of those weird problems you get with Wintel laptops. Don't know anything about writable DVDs, though.

If I were you, I'd go with Linux, if you're comfortable there, and run VMWare if you require some Windows application. VMWare really does work very well under Linux. Perhaps better than under Windows. Macs are also very nice and would tend to have a little more application support than Linux. You can also get VirtualPC, which runs quite well, too, though not as well as VMWare does (but better, really, when you consider that it's actually emulating to some extent and not just virtualizing the CPU). I've considered in the past setting up Windows in VMWare and making it a nonpersistent disk after installing all the appropriate software and saving all data to a network drive. That way, your installation will never get corrupted.

Regardless, you'll be better off than with a Windows machine as it won't start to break down in 6 months.