Run osu! after rebooting. This might be helpful?
EDIT:
After that, 2nd attempt to run osu was successful.
EDIT2: This time, osu! works fine, though still some issues remain.
EDIT3: Oct. 29th: Running osu! always fails with the first attempt after rebooting. since second attempt it works well.
SPOILER
12. 10. 28. 오후 12:08:59.100 Wineskin[421]: Starting up...
12. 10. 28. 오후 12:08:59.101 Wineskin[421]: reading all configuration information...
12. 10. 28. 오후 12:08:59.148 Wineskin[421]: Starting up WineskinX11
12. 10. 28. 오후 12:08:59.164 Wineskin[421]: Using Engine WS9Wine1.5.15
12. 10. 28. 오후 12:08:59.642 Wineskin[452]: Starting up...
12. 10. 28. 오후 12:08:59.642 Wineskin[452]: reading all configuration information...
12. 10. 28. 오후 12:08:59.661 Wineskin[452]: files passed in to open, will open with associated app
12. 10. 28. 오후 12:08:59.675 Wineskin[452]: Starting specified executable in Wine
12. 10. 28. 오후 12:08:59.852 WindowServer[96]: Received display connect changed for display 0x4272d80
12. 10. 28. 오후 12:08:59.884 WindowServer[96]: Received display connect changed for display 0x3f003d
12. 10. 28. 오후 12:08:59.884 WindowServer[96]: Received display connect changed for display 0x3f003e
12. 10. 28. 오후 12:08:59.885 WindowServer[96]: CGXMuxAcknowledge: Posting glitchless acknowledge
12. 10. 28. 오후 12:08:59.916 CVMServer[132]: Check-in to the service com.apple.cvmsCompAgent_x86_64 failed. This is likely because you have either unloaded the job or the MachService has the ResetAtClose attribute specified in the launchd.plist. If present, this attribute should be removed.
12. 10. 28. 오후 12:08:59.944 WindowServer[96]: MPAccessSurfaceForDisplayDevice: Set up page flip mode on display 0x04272d80 device: 0x1040ca320 isBackBuffered: 1 numComp: 3 numDisp: 3
12. 10. 28. 오후 12:09:00.009 WindowServer[96]: Received display connect changed for display 0x4272d80
12. 10. 28. 오후 12:09:00.052 CVMServer[132]: Check-in to the service com.apple.cvmsCompAgent_x86_64 failed. This is likely because you have either unloaded the job or the MachService has the ResetAtClose attribute specified in the launchd.plist. If present, this attribute should be removed.
12. 10. 28. 오후 12:09:00.917 Wineskin[421]: Wrapper Bundle running on PID 436
12. 10. 28. 오후 12:09:00.918 Wineskin[421]: WineskinX11 running on PID 450
12. 10. 28. 오후 12:09:04.046 Wineskin[421]: Starting specified executable in Wine
12. 10. 28. 오후 12:09:04.000 kernel[0]: process 475 set trusted
12. 10. 28. 오후 12:09:04.000 kernel[0]: process 482 set trusted
12. 10. 28. 오후 12:09:04.901 Wineskin[452]: Wineserver running on PID 535
12. 10. 28. 오후 12:09:05.252 Wineskin[421]: Wineserver running on PID 535
12. 10. 28. 오후 12:09:05.253 Wineskin[421]: Sleeping and monitoring from the background while app runs...
12. 10. 28. 오후 12:09:22.891 mdworker[609]: Unable to talk to lsboxd
12. 10. 28. 오후 12:09:23.000 kernel[0]: Sandbox: sandboxd(645) deny mach-lookup com.apple.coresymbolicationd
12. 10. 28. 오후 12:09:23.289 sandboxd[645]: ([609]) mdworker(609) deny mach-lookup com.apple.ls.boxd
12. 10. 28. 오후 12:09:24.000 kernel[0]: process 609 set trusted
12. 10. 28. 오후 12:09:24.000 kernel[0]: process 608 set trusted
EDIT:
After that, 2nd attempt to run osu was successful.
SPOILER
12. 10. 28. 오후 12:09:59.736 Wineskin[421]: Application finished, cleaning up and shut down...
12. 10. 28. 오후 12:09:59.788 WindowServer[96]: Received display connect changed for display 0x4272d80
12. 10. 28. 오후 12:09:59.813 WindowServer[96]: CGXMuxAcknowledge: Posting glitchless acknowledge
12. 10. 28. 오후 12:09:59.835 WindowServer[96]: Received display connect changed for display 0x4272d80
12. 10. 28. 오후 12:09:59.835 WindowServer[96]: Received display connect changed for display 0x3f003d
12. 10. 28. 오후 12:09:59.835 WindowServer[96]: Received display connect changed for display 0x3f003e
12. 10. 28. 오후 12:09:59.843 Wineskin[421]: Finished!
12. 10. 28. 오후 12:10:01.675 Safari[208]: CGContextClipToRect: invalid context 0x0
12. 10. 28. 오후 12:10:14.000 kernel[0]: process 857 set trusted
12. 10. 28. 오후 12:10:14.000 kernel[0]: revoking trust for process 411
12. 10. 28. 오후 12:10:24.000 kernel[0]: revoking trust for process 608
12. 10. 28. 오후 12:10:24.000 kernel[0]: revoking trust for process 609
12. 10. 28. 오후 12:10:44.000 kernel[0]: revoking trust for process 482
12. 10. 28. 오후 12:11:09.999 Wineskin[861]: Starting up...
12. 10. 28. 오후 12:11:10.000 Wineskin[861]: reading all configuration information...
12. 10. 28. 오후 12:11:10.012 Wineskin[861]: Starting up WineskinX11
12. 10. 28. 오후 12:11:10.013 Wineskin[861]: Using Engine WS9Wine1.5.15
12. 10. 28. 오후 12:11:10.220 Wineskin[891]: Starting up...
12. 10. 28. 오후 12:11:10.221 Wineskin[891]: reading all configuration information...
12. 10. 28. 오후 12:11:10.228 Wineskin[891]: files passed in to open, will open with associated app
12. 10. 28. 오후 12:11:10.243 Wineskin[891]: Starting specified executable in Wine
12. 10. 28. 오후 12:11:10.331 WindowServer[96]: Received display connect changed for display 0x4272d80
12. 10. 28. 오후 12:11:10.362 WindowServer[96]: Received display connect changed for display 0x3f003d
12. 10. 28. 오후 12:11:10.362 WindowServer[96]: Received display connect changed for display 0x3f003e
12. 10. 28. 오후 12:11:10.363 WindowServer[96]: MPAccessSurfaceForDisplayDevice: Set up page flip mode on display 0x04272d80 device: 0x1040ca320 isBackBuffered: 1 numComp: 3 numDisp: 3
12. 10. 28. 오후 12:11:10.369 WindowServer[96]: CGXMuxAcknowledge: Posting glitchless acknowledge
12. 10. 28. 오후 12:11:10.410 WindowServer[96]: Received display connect changed for display 0x4272d80
12. 10. 28. 오후 12:11:11.681 Wineskin[861]: Wrapper Bundle running on PID 875
12. 10. 28. 오후 12:11:11.682 Wineskin[861]: WineskinX11 running on PID 889
12. 10. 28. 오후 12:11:11.969 Wineskin[861]: Starting specified executable in Wine
12. 10. 28. 오후 12:11:12.049 Wineskin[861]: Wineserver running on PID 957
12. 10. 28. 오후 12:11:12.049 Wineskin[861]: Sleeping and monitoring from the background while app runs...
12. 10. 28. 오후 12:11:12.374 Wineskin[891]: Wineserver running on PID 957
12. 10. 28. 오후 12:11:14.000 kernel[0]: process 936 set trusted
EDIT2: This time, osu! works fine, though still some issues remain.
EDIT3: Oct. 29th: Running osu! always fails with the first attempt after rebooting. since second attempt it works well.