Observation shows that some Windows softwares run perfectly on Wine and some just fail miserably. Rather than trying them out randomly, I wanted to create a place where we can have some ideas about Wine-suitable, and -unsuitable, softwares.
So, exactly which areas of Windows operating systems does Wine fully support or still show weaknesses? By implication, what are the kinds of Windows applications that are guaranteed to run without flaws on Wine?
You should check out the Wine App Database, it lists programs that have been tested on Wine, along with test results.
http://appdb.winehq.org/
Some programs work great, some don't, some require patches or dirty fixes e.g. Winetricks. Luck of the draw really. Either way the App DB is great as it contains reports on Windows applications that have been tested and detail how successful the program was on a specific distro.
It might not have all the Windows programs in the world, but it certainly lists most of the mainstream Windows applications.
In a perfect world, the Wine devs would be able to follow a fixed specification with which to build a fully binary compatible replacement for Windows. But this is not the case. They know the public APIs and know what those APIs are supposed to do. Everything else (ie how they do it) is educated guesswork.
The ideal would also involve Windows functioning consistently, which it does not. Parts have been bolted onto very old code. Application developers can work around those bugs when they're building their apps but it also means that Wine has to follow everything, even the quirks and often by trial and error (users submitting bugs for specific applications).
Nothing is guaranteed to run. Even things that work perfectly, even better than native, are not guaranteed to remain that way. Often in the Wine world, in order to fix something, you have to break half a dozen other things... You just hope you (or somebody else) finds those new bugs before the code hits a stable release.
If you want long term stable support for a batch of applications, look at the commercial arm of Wine: CrossOver.
The compatibility of Wine with windows software varies based on the software and which version of windows it was intended to run on.
Wine App Database has a great index of software and its level of compatibility with varying versions of Wine and Linux distribution. Of course not all applications are reported nor is the status of those applications always up to date.
There are also commercial products derived from Wine such as Crossover, and Cedega (although outdated).
Now that a Direct3d 10 & 11 is going to be natively supported in linux we can expect much more reliability and performance in many more games.
www.codeweavers.com/
www.transgaming.com/
www.phoronix.com/scan.php?page=article&item=mesa_gallium3d_d3d11
To make sweeping generalizations:
Games tend to be poorly supported under wine. Things sorta work, almost work, but then usually fail miserably. There are a few rare standouts, but as a rule, I'm pessimistic about running any given game under wine.
On the other hand, small "application-type" programs tend to function quite well. Tools for doing a single thing usually function, whether it's converting a data format, displaying a file, or doing some other single function. In general, if the whole app is under 10 megs, it's quite likely to work.
Where application support tends to break down is when you get into larger projects that have a lot of legacy code.
There is also the possibility to use Mono for windows programs that are written in .NET. Search for it and install it. To use, just run
mono ProgramName