I want to run a Windows application in Ubuntu using Wine. However, from past experience I know that this can be a frustrating, difficult process because of Wine and hardware bugs. What is the best, canonical way to troubleshoot problems I encounter trying to install and run a given application?
I recommend checking out the Wine HQ AppsDB.
They categorize apps by compatibility. Reviews include Wine version and Linux distro (and version) the app was tested on, so you may have more success than indicated in old reviews.
In my experience, Wine has been pretty good for my windows apps needs. Generally, it's not very good at running commercial equivalents to the big stock apps in Ubuntu (it's always tricky to install Internet Explorer, MS Office, Adobe Photoshop, at least their latest versions, in Wine). Some apps run flawlessly, whereas a lot of apps need just a hint of tweaking (missing DLL or font file, some apps try to run from CD). Compatibility for most apps improves with every new version of Wine. Best check out the apps DB, you could ask here again or take it to the forums. Good luck!