Yes, I have, but nothing major. Only a few small utilities that were needed. For example, the Xnet usage monitor application works. After Wine is installed, you just double click on the .EXE file. You see the normal Windows installer sreen. It installs itself (Wine keeps all programs nicely organised in one folder, which pretends to be a C: drive as far as the Windows apps is concerned) and then you can run it. The Windows-styled buttons and GUI look and feel of those Windows apps looks a bit out of place on a Gnome or KDE desktop, of course, but that is to be expected.
Another application I ran was a custom image viewer that came with a CD of specialised image material I had ordered. At first I was shocked that they had the images all in some proprietary database with a Windows-only viewer application, but I was able to run it under Wine without problem. Fortunately, the application allowed me to save the images as JPGs, so that I could do further work on them through GNU/Linux tools. But even here: Insert the CD, double click on the "setup.exe" file and it installed itself and ran just fine.
I think the issue is this: If the program is 'simple' it will work nicely. If it does some deep magic with video drivers and on-the-fly-hack-the-OS kind of stuff, it might be less likely to work.
But to say WINE can run some pretty good and advanced software (and a handful of games too), but support can also vary across distributions and versions, so sometimes it's a hit and miss situation.
You can also check out the App Database list to see if the software you're after works or not.
I've tried WINE with around 3 apps, and worked for only 1, the other failed to launch and another launched setup but never completed successfully. But as said before, simple apps should work perfectly fine.
Yup that's basically the long and short of it. There are a hell of a lot of Apps that work these days in Wine but they are very much "by popular demand" The Wine team is a pretty busy one,
I mean think about the logic of writing a program, that runs other programs, which are closed source (No access to the code they're written in), designed to work on a completely different operating system, which is not only closed source, but in fact the code is so closely guarded that it is believed Cerberos himself guards it at the gates of hell, That's not really an easy task now is it? lol
Because of this only the most popular/most requested programs work in Linux, Counter Strike Source and HL2 for example, WoW and BF2 etc etc, then utilities like CS2 Photoshop and Dreamweaver etc work well because they've had a LOT of time put into them in order to get them working, purely because the demand was high.
The main thing to do if you're considering a swap to Linux is not to look at what programs will work in Wine but instead to look for Linux alternatives, granted Dreamweaver CS3 is by far the best WYSIWYG on the planet to date for web editing but it still isn't as good as actually uploading it and viewing the result for yourself, especially when you consider that it will only predict how IE7 will show the code, it won't allow for Firefox, Opera, Chrome, Navigator, Flock etc etc etc and how they will display your code.
We use Dreamweaver here for designing a web site, then upload and test in all the various browsers and go through editing the code, adding the hacks and re-write rules for all the various browsers etc.
There's a whole world of free software out there, which is completely open source (Not that this matters to a lot of every day users who are not programmers) but at the end of the day it's still FREE both "As in Beer" and "As in Speech" and it will do the same or a better job than a lot of the software you have to pay through the nose for.
Sorry about the length of this but there's a lot to be said when it comes to open source vs proprietary and Linux vs Windows etc, it all comes down to personal choice and how much you really want the end result of being "Windows Free".