Well I'm trying to run this through wine again (I must be a masochist). Instead of using the GUI, I used the command line to get wine and winetricks working on OS X, and installed the corefonts and dotnet20 winetricks. Then I copied my game folder over and ran it. The crash / bug reporter screen shows up for me. I'm not sure if I'm missing anything, but any help would be much appreciated. Basically it crashes then submits the bug and restarts and the same thing happens. I also tried deleting my user configuration. I have attached a screen shot.
CoGetContextToken apartment not initialised
fixme:shell:URL_ParseUrl failed to parse L"System"
fixme:shell:URL_ParseUrl failed to parse L"System.Windows.Forms"
fixme:shell:URL_ParseUrl failed to parse L"System.Drawing"
fixme:shell:URL_ParseUrl failed to parse L"osu"
fixme:shell:URL_ParseUrl failed to parse L"Microsoft.Xna.Framework"
fixme:shell:URL_ParseUrl failed to parse L"System.Runtime.Remoting"
fixme:process:SetProcessPriorityBoost (0x170,0): stub
fixme:shell:URL_ParseUrl failed to parse L"msvcm80"
fixme:win:EnumDisplayDevicesW ((null),0,0x33dba0,0x00000000), stub!
fixme:wave:wodDsCreate DirectSound not implemented
fixme:wave:wodDsCreate The (slower) DirectSound HEL mode will be used instead.
fixme:wave:wodDsCreate DirectSound not implemented
fixme:wave:wodDsCreate The (slower) DirectSound HEL mode will be used instead.
err:ole:CoGetClassObject class {bcde0395-e52f-467c-8e3d-c4579291692e} not registered
err:ole:CoGetClassObject no class object {bcde0395-e52f-467c-8e3d-c4579291692e} could be created for context 0x1
err:wgl:opengl_error No OpenGL support compiled in.
err:d3d_caps:WineD3D_CreateFakeGLContext Can't find a suitable iPixelFormat.
err:d3d:InitAdapters Failed to get a gl context for default adapter
err:d3d:WineDirect3DCreate Direct3D9 is not available without opengl
fixme:shell:URL_ParseUrl failed to parse L"mscorlib.resources"
fixme:shell:URL_ParseUrl failed to parse L"osu!.resources"
fixme:shell:URL_ParseUrl failed to parse L"{ef5dc3ce-33e8-49bf-a83b-f70d0ebf15b8}"
fixme:shell:URL_ParseUrl failed to parse L"osu!.resources"
fixme:advapi:CheckTokenMembership (0x440 0x21bb40 0x11dbdb48) stub!
fixme:imm:ImmDisableIME (-1): stub
fixme:thread:NtQueryInformationThread Cannot get kerneltime or usertime of other threads
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:advapi:RegisterEventSourceW ((null),L".NET Runtime 2.0 Error Reporting"): stub
fixme:advapi:ReportEventW (0xcafe4242,0x0001,0x0000,0x000003e8,0x0,0x0008,0x000000d0,0x3009a1b4,0x6cd260): stub
err:eventlog:ReportEventW L"osu!.exe"
err:eventlog:ReportEventW L"1.3.3.7"
err:eventlog:ReportEventW L"4ae3fa5f"
err:eventlog:ReportEventW L"unknown"
err:eventlog:ReportEventW L"0.0.0.0"
err:eventlog:ReportEventW L"00000000"
err:eventlog:ReportEventW L"0"
err:eventlog:ReportEventW L"8000000a"
fixme:advapi:DeregisterEventSource (0xcafe4242) stub
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet
fixme:thread:NtQueryInformationThread info class 9 not supported yet