I've installed WLM 2008 on my Ubuntu 9.10 AMD64 with POL. My system language is Italian.
The menu icons (either in Gnome menu and in Wine menu) didn't work at all.
By running the command /usr/share/playonlinux/playonlinux --run "Windows Live Messenger" I got:
Checking python : [ Ok ]
Windows Live Messenger: riga 5: cd: /home/<myname>/.PlayOnLinux/wineprefix/WLM2008/drive_c/Program Files/Windows Live/Messenger: Nessun file o directory
wine: could not load L"C:\\\\windows\\\\system32\\\\msnmsgr.exe": Module not found (The first error message means "[...] line 5 [...] No such file or directory")
I created a symlink from "/home/<myname>/.PlayOnLinux/wineprefix/WLM2008/drive_c/Program Files" to my program files localized directory "/home/<myname>/.PlayOnLinux/wineprefix/WLM2008/drive_c/Programmi" and everything went right.
So it seems a problem with localization that probably appears in some other application install script.
Also, I got the French version of WLM. IMO the user should be able to choose the right version, or it should be installed the English one. (Maybe I did something wrong?)