Hey, I have the same problem, and I'm using POM as well, but I'm using High Sierra.
I found my console, hope you can help
[04/04/20 12:07:53] - Running wine-3.16 --version (Working directory : /Applications/PlayOnMac.app/Contents/Resources/playonlinux/python)
wine-3.16
PlayOnMac logfile
-------------------
Date: 04/04/20 12:07:53
> PlayOnMac Version
4.3.4
> uname -a
Darwin eshwars-mbp.lan 17.7.0 Darwin Kernel Version 17.7.0: Thu Jun 21 22:53:14 PDT 2018; root:xnu-4570.71.2~1/RELEASE_X86_64 x86_64
> lsb_release -a
> wine --version
wine-3.16
> POL_WINEVERSION
3.16
> WINEPREFIX
/Users/eshwarsarey/Library/PlayOnMac//wineprefix/PCBuildingSimulator
> Distribution
10.13.7 (17.7.0)
> glxinfo \| grep rendering
> glxinfo \| grep renderer
> OpenGL libs (Direct rendering testing)
[04/04/20 12:08:19] - Running wine-3.16 cmd /c echo %ProgramFiles% (Working directory : /Applications/PlayOnMac.app/Contents/Resources/playonlinux/python)
dbus[5638]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
C:\Program Files (x86)
[04/04/20 12:08:25] - ----- Starting function POL_Function_SetResolution -----
[04/04/20 12:08:38] - Running wine-3.16 regedit /Users/eshwarsarey/Library/PlayOnMac//tmp/regkey.reg (Working directory : /Users/eshwarsarey/Library/PlayOnMac/tmp)
[04/04/20 12:08:38] - Content of /Users/eshwarsarey/Library/PlayOnMac//tmp/regkey.reg
-----------
REGEDIT4
[HKEY_CURRENT_USER\Software\Wine\X11 Driver]
"Desktop"="1024x600"
-----------
dbus[5757]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
[04/04/20 12:08:40] - Running wine-3.16 regedit /Users/eshwarsarey/Library/PlayOnMac//tmp/regkey.reg (Working directory : /Users/eshwarsarey/Library/PlayOnMac/tmp)
[04/04/20 12:08:40] - Content of /Users/eshwarsarey/Library/PlayOnMac//tmp/regkey.reg
-----------
REGEDIT4
[HKEY_CURRENT_USER\Software\Wine\Explorer\Desktops]
"Default"="1024x600"
-----------
[04/04/20 12:08:41] - Running wine-3.16 regedit /Users/eshwarsarey/Library/PlayOnMac//tmp/regkey.reg (Working directory : /Users/eshwarsarey/Library/PlayOnMac/tmp)
[04/04/20 12:08:41] - Content of /Users/eshwarsarey/Library/PlayOnMac//tmp/regkey.reg
-----------
REGEDIT4
[HKEY_CURRENT_USER\Software\Wine\Explorer]
"Desktop"="Default"
-----------
[04/04/20 12:08:43] - ----- Ending function POL_Function_SetResolution -----
[04/04/20 12:08:44] - ----- Starting function POL_Install_vcrun2010 -----
[04/04/20 12:08:44] - Running wine-3.16 start /unix vcredist_x64.exe /q (Working directory : /Users/eshwarsarey/Library/PlayOnMac/ressources/vcrun2010)
dbus[5988]: Dynamic session lookup supported but failed: launchd did not provide a socket path, verify that org.freedesktop.dbus-session.plist is loaded!
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
0024:err:ntoskrnl:IoCreateDriver failed to insert driver L"\\Driver\\WineHID" in tree
002c:fixme:clusapi:GetNodeClusterState ((null),0x33ec34) stub!
002c:fixme:ntdll:server_ioctl_file Unsupported ioctl 70000 (device=7 access=0 func=0 method=0)
002c:fixme:ntdll:server_ioctl_file Unsupported ioctl 70000 (device=7 access=0 func=0 method=0)
002c:fixme:ntdll:server_ioctl_file Unsupported ioctl 70000 (device=7 access=0 func=0 method=0)
002c:fixme:advapi:DecryptFileA ("c:\\1c515ac477a347f3349fa0e6d1\\", 00000000): stub