Windows 7 has been out for almost a week and the horror stories seem relatively few and far between. Maybe you're thinking it's time to take the plunge? I did four upgrades last weekend, all of them 'clean' installs (your only choice unless you're upgrading from Vista) and found the actual upgrade didn't take very long. The time consuming part was backing everything up and then reinstalling apps.
One real time saver (for you, if not for your computer) in this last step is using Ninite. This is a free service that automates installation of a selection of free applications. Go to the site, tick off all the apps you want, then click the Get Installer button. A small 'stub' file gets downloaded to your system. Run that, and go have lunch or something (though my partner thinks the name implies doing the install overnight; she pronounces it like a small child saying 'ni-night' before going to bed). When you come back, all your apps are installed and waiting. Ninite doesn't leave any traces of itself on your system; once these apps are installed there's no indication (that I've been able to find) that the installation was automated.
I didn't actually compare the time it took for Ninite to download and install everything to the time it would take me to download and install each application separately, but the real savings here is in your time. You can go work on something else while Ninite does the unattended installs. If you've got a bunch of systems to do and access to network storage, you can set up a local network cache of the apps which should save a lot of time in subsequent installs. I didn't test this feature, but you can find some details on the Advanced Features page.
The only downsides to using Ninite are that you're limited to the apps offered (though there's a form available to suggest apps to add) and that the installations all happen in default locations (c:\program files usually). Of course if Ninite asked you a bunch of questions for each app it'd cut down the convenience factor, so I'm not sure that's a downside.
I've recommended Ninite to a few friends who were installing Windows 7 and they've used it with the same good results that I've had. There's something liberating about a brand new installation of Windows. If you try a service like Ninite and things go wrong, you can just re-do the upgrade; all you've lost is the 30-45 minutes of time the upgrade takes. I'm not as comfortable recommending the service for use on an in-use production machine without doing more testing (though I hasten to add that I've seen nothing to indicate it would cause any problems). It isn't often that you have a sudden need to install a bunch of new apps on an in-use machine anyway, so that caveat may be moot.