Windows 7 is a cluttered mess
Before some commenter puts his foot in his mouth by suggesting an upgrade of the legacy app, I'll point out that it's not broken; it's fully functional; a replacement would have to be commissioned at a great deal of pointless, wasteful expense. Besides, getting it to work was the least of the problems he faced, and it was solved by installing the open-source DOSBox virtual machine, complete with the open-source FreeDOS operating system (which is included with DOSBox).
Basically, what I've found from the "experience" is that whatever benefits are to be had from Windows 7 on a technical basis are completely eclipsed by the astoundingly bad user interface. I put "experience" in quotes because Microsoft sets great store by the user experience. Sadly, they've managed to screw it up royally with this release. I find it to be a cluttered mess.
Part of it is the brain-dead options. Part of it is Windows 7 constantly trying to guess my intent, and failing in every single instance. Part of it is the haphazard and confusing UI. And it's not a matter of simply not being flexible or "familiar" on my part. I'm used to a wide range of UIs, including, a plain terminal, OS/400, all preceding versions of Windows and DOS, OS/2, KDE, GNOME... even GEM and the Amiga Workbench. Some of these are good, some bad, but Windows 7 sets a new standard for the sheer effort that went into its failure. The machine is a Dell Vostro desktop, and my criticisms are written specifically about the default settings of Windows 7 as they appear straight from the OEM. Keep in mind that nothing prevented me from actually getting the work done, but "the UI experience" was FAR from satisfactory.
Setting up a network has always been more difficult on Windows than on other platforms, but this experience was just silly. I wish Microsoft would simply stop screwing with their network protocols every bloody release and settled on something like NFS. It simply works reliably and securely, and has for 25 years.
Libraries are a reasonable idea gone horribly bad. Read this Microsoft Team Blog to learn the rationale behind them. The bottom line is that you previously chose to put files exactly where you wanted them rather than where Microsoft wanted you to put them. They imagine that your search "experience" is damaged by your lack of desire for any search experience whatsoever, and they then conclude that you really wanted to put them where Microsoft wants them and not where you do. Your lack of desire for their useless CPU cycle-wasting indexing function is some sort of derangement on your part. They "correct" this by providing a virtual folder that contains the stuff that's in their chosen location as well as your chosen locations. Now they can go ahead and index all the stuff you didn't want indexed, but should have if you were sane and living in Redmond.
In practice, a library looks just like Google's Picasa... a bunch of files grouped by folder in a big honkin' scrollable window. In fact, if you didn't know the godlike extent of Microsoft's innovative powers, you could reasonably conclude that they ripped off the feature from Google. The fact that they copied it doesn't necessarily make it good... I tried Picasa as well and I can't say I enjoyed it at all. It was a cluttered mess there, and it's a cluttered mess in Windows Explorer.
Nevertheless, Windows 7 users are intended to go to Libraries in order to manage their documents, music, pictures, and other files. This can make for a bit of confusion and difficulty when a user wants to save content. The user expects it to go in the place indicated, and it doesn't. This is further complicated by Windows 7's insistence on trying to second-guess your decisions. For instance, if you're trying to put a file into a location Windows has restricted, you're told that you don't have the proper rights... would you like to put it in Timbuktu instead? If you click "no," meaning "No, I don't want it in Timbuktu... I want it here," your reasonable expectation would be that you are given an opportunity to provide sufficient credentials to save the document exactly where you wanted it. That doesn't happen.
Furthermore, libraries require you to index the files. So if you imagine you might just turn off the indexing service and do your part against Global Warming, forget it. You're going to burn those cycles anyway.
Your average user will be stymied by trying to change a file's type. Really, now, how hard would it be to put in an option on the context menu or in the properties dialog to simply change the file type? You could call it... oh, I dunno... "Change File Type". Microsoft believes it shouldn't ever be necessary, so they hide it under the dustbin, unnecessarily. Here's how it's done.
The command prompt (cmd) never actually displayed on the screen. These instructions never worked on that box. It was displayed in search results, and a subsequent shutdown claimed it was running, but it was never visible or accessible in any way. Fortunately, on my USB flash drive I carry a portable command prompt that I used with success.
In general, I found it much easier and more productive to simply forget almost the entire Windows 7 user interface, and use the excellent xplorer2 utility instead. Xplorer2 works exactly as expected, and has the advantage of a dual-pane interface to facilitate file moves and copies. This is the single feature that would most improve Windows Explorer, but 15 years after introducing Windows 95, Microsoft still hasn't adopted it. Hmph.
Speaking with other Windows 7 users didn't reveal any great love for it in this neighborhood. Basically, people are pissed at much the same things that I am, and aren't really thrilled with the changes to Microsoft Office, either.
My personal opinion? Microsoft's Windows 7 makes Ubuntu Linux look GREAT. In addition to having higher security than Vista, it has the ease of use I haven't been able to get out of any Microsoft OS without having to install something like xplorer2. On top of that, the application repositories makes the "experience" of installing programs superior to that of any Microsoft product ever. And the included OpenOffice.org acts exactly as it should. I'm biased, because I've liked Linux for a long time (My preference is Kubuntu), but the users I've shown Ubuntu to have preferred it to the newer Microsoft OSes, hands down.
Of course, you can download a run-live CD image from the Ubuntu website, but here's another nifty way to run it: get VirtualBox from Sun Microsystems (it's free) and run a virtual image. That way you can run Ubuntu at the same time as Windows and really get an apples-to-apples comparison. Here's the latest: (link).