https://bugs.winehq.org/show_bug.cgi?id=39294
--- Comment #10 from Albert Flügel af@muc.de --- Latest findings: I tested with these iTunes versions: 12.1.2.27, 12.2.2.25, 12.3.1 (current one) and wine 1.7.39-1.7.55
The 12.2 and 12.3 version of iTunes i never get to run. Always tried with .wine removed. Even the debugger does not produce output in the "Program Error Details" window.
iTunes 12.1.2.27 works with all wine versions one time with a fresh .wine directory. At second start it crashes. When i remove the file .wine/drive_c/users/myname/Application Data/Apple Computer/iTunes/iTunesPrefs.xml it starts again and i have to confirm the license. So at least this version would start, but hicks up reading the xml file. However some months ago it worked continuously, so there must be other conditions around breaking the program. I moved all other directories named iTunes or whatever out of the way, but nothing helped. So i don't see any use in regressions as the problem has not been introduced by a wine version, like stated in an earlier comment.