I am also having the same problem. Looking at the wineprefix for Guitar Rig it looks like there's a log file which may provide useful information to get this issue resolved (sorry for the long post, wish this forum had a minimizable code block or smthg).
[08/20/16 21:51:35] - Running wine-1.5.20 --version (Working directory : /home/jonathan/.PlayOnLinux/shortcuts)
wine-1.5.20
PlayOnLinux logfile
-------------------
Date: 08/20/16 21:51:35
> PlayOnLinux Version
4.2.10
> uname -a
Linux jonathan-Z97X-Gaming-5 4.4.0-34-generic #53-Ubuntu SMP Wed Jul 27 16:06:39 UTC 2016 x86_64 x86_64 x86_64 GNU/Linux
> lsb_release -a
> wine --version
wine-1.5.20
> POL_WINEVERSION
1.5.20
> WINEPREFIX
/home/jonathan/.PlayOnLinux//wineprefix/GuitarRig5
> Distribution
Ubuntu 16.04.1 LTS
> glxinfo \| grep rendering
direct rendering: Yes
> glxinfo \| grep renderer
GLX_MESA_multithread_makecurrent, GLX_MESA_query_renderer,
GLX_MESA_multithread_makecurrent, GLX_MESA_query_renderer,
Extended renderer info (GLX_MESA_query_renderer):
OpenGL renderer string: Mesa DRI Intel(R) Haswell Desktop
> OpenGL libs (Direct rendering testing)
check_dd_x86 missing, test skipped
check_dd_amd64 missing, test skipped
[08/20/16 21:51:42] - Running wine-1.5.20 cmd /c echo %ProgramFiles% (Working directory : /home/jonathan/.PlayOnLinux/shortcuts)
C:\Program Files
[08/20/16 21:51:45] - Running wine-1.5.20 regedit /home/jonathan/.PlayOnLinux//tmp/regkey.reg (Working directory : /home/jonathan/.PlayOnLinux/shortcuts)
[08/20/16 21:51:45] - Content of /home/jonathan/.PlayOnLinux//tmp/regkey.reg
-----------
REGEDIT4
[HKEY_CURRENT_USER\Software\Wine]
"Version"="winxp"
-----------
[08/20/16 21:51:45] - Running wine-1.5.20 regedit /home/jonathan/.PlayOnLinux//tmp/regkey.reg (Working directory : /home/jonathan/.PlayOnLinux/shortcuts)
[08/20/16 21:51:45] - Content of /home/jonathan/.PlayOnLinux//tmp/regkey.reg
-----------
REGEDIT4
[HKEY_CURRENT_USER\Software\Wine\Direct3D]
"DirectDrawRenderer"="gdi"
-----------
[08/20/16 21:52:02] - Running wine-1.5.20 /media/guitar-rig/setup.exe (Working directory : /home/jonathan/.PlayOnLinux/shortcuts)
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
err:richedit:ReadStyleSheet skipping optional destination
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:storage:create_storagefile Storage share mode not implemented.
fixme:ntdll:server_ioctl_file Unsupported ioctl 9c040 (device=9 access=3 func=10 method=0)
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:ntdll:server_ioctl_file Unsupported ioctl 9c040 (device=9 access=3 func=10 method=0)
fixme:ntdll:server_ioctl_file Unsupported ioctl 9c040 (device=9 access=3 func=10 method=0)
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:storage:create_storagefile Storage share mode not implemented.
fixme:ntdll:server_ioctl_file Unsupported ioctl 9c040 (device=9 access=3 func=10 method=0)
fixme:win:RegisterDeviceNotificationW (hwnd=0x147768, filter=0xb2e988,flags=0x00000005) returns a fake device notification handle!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:ntdll:server_ioctl_file Unsupported ioctl 9c040 (device=9 access=3 func=10 method=0)
fixme:ntdll:server_ioctl_file Unsupported ioctl 9c040 (device=9 access=3 func=10 method=0)
fixme:storage:create_storagefile Storage share mode not implemented.
fixme:ntdll:server_ioctl_file Unsupported ioctl 9c040 (device=9 access=3 func=10 method=0)
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:win:LockWindowUpdate ((nil)), partial stub!
fixme:ntdll:server_ioctl_file Unsupported ioctl 9c040 (device=9 access=3 func=10 method=0)
fixme:ntdll:server_ioctl_file Unsupported ioctl 9c040 (device=9 access=3 func=10 method=0)
fixme:win:UnregisterDeviceNotification (handle=0xcafeaffe), STUB!
[08/20/16 21:52:50] - Running wine-1.5.20 winepath -u C:\\users\\jonathan\\Desktop (Working directory : /home/jonathan/.PlayOnLinux/shortcuts)
fixme:win:RegisterDeviceNotificationW (hwnd=0x147e10, filter=0xb2e988,flags=0x00000005) returns a fake device notification handle!
/home/jonathan/.PlayOnLinux//wineprefix/GuitarRig5/dosdevices/c:/users/jonathan/Desktop
fixme:win:UnregisterDeviceNotification (handle=0xcafeaffe), STUB!
[08/20/16 21:53:06] - ----- Starting function POL_Install_wineasio -----
[08/20/16 21:53:07] - Running wine-1.5.20 regsvr32 /home/jonathan/.PlayOnLinux//wine/linux-x86/1.5.20/lib/wine/wineasio.dll.so (Working directory : /home/jonathan/.PlayOnLinux/tmp)
fixme:win:RegisterDeviceNotificationW (hwnd=0x147e10, filter=0xb2e988,flags=0x00000005) returns a fake device notification handle!
Failed to load DLL /home/jonathan/.PlayOnLinux//wine/linux-x86/1.5.20/lib/wine/wineasio.dll.so
fixme:win:UnregisterDeviceNotification (handle=0xcafeaffe), STUB!
[08/20/16 21:53:36] - Running wine-1.5.20 wineconsole cmd (Working directory : /usr/share/playonlinux/python)
fixme:win:RegisterDeviceNotificationW (hwnd=0x147e10, filter=0xb2e988,flags=0x00000005) returns a fake device notification handle!
err:wineconsole:WCUSER_SetFont wrong font
err:wineconsole:WCUSER_SetFont wrong font