http://bugs.winehq.org/show_bug.cgi?id=10002
--- Comment #13 from Dan Kegel dank@kegel.com 2008-10-09 07:56:04 --- You can avoid the first error dialog and get to the second more quickly by moving Plugins/Extensions out of the way; evidently it's having trouble loading a plugin.
The second dialog, about two missing required plugins, is discussed in several places, e.g. http://www.adobeforums.com/webx/.3c0583da There they say it can be caused by a missing font, or by a corrupt AiPrefs file. I think that would be in ~/.wine/drive_c/windows/profiles/$LOGNAME/Application Data/Adobe/Adobe Illustrator CS2 Settings but I don't see it. Deleting that folder, as suggested by some adobe users, doesn't help; Illustrator does recreate it, but it neither creates an aiprefs file nor successfully starts.
The app *does* look for that file. Touching AIPrefs in that directory causes the app to find and open the file, but that doesn't help.