I wanted to update this thread in case someone (like me) wanted to know what's the state of wine + MWLL in 2020
So . . . test on Mac with PlayOnMac (wine) and it works once you find a stable configuration. Before someone asks, my SSD is too small to host a windows installation and yes, I did install windows bootable on external hard disk but it's slow and painful and no I dont want to use a pirated version of windows so after 30 days the windows installation would be unusable.
So here's what worked for me:
1. Add new 32bit space
2. Wine version 4.19-staging
3. Wine set to Windows 7
4. Installed from winetricks directx9, dotnet40, mfc42 (I dont think it's necessary), msvc80, msxml6, vcrun2005. Some of those probably are not needed
5. Installed MWLL launcher (60MB circa), the one that you find on the main page
6. DO NOT UPDATE THE LAUNCHER from version 3.0 to 3.2 cause it will stop working (at least for me)
7. Open launcher and install games data, if it's stuck for too long you might want to force close everything, check that there's no other wine related processes in the mac activity monitor and if any kill them all.
8. Optional (click the wrench/hammer icon, top right icon) and "Repair install" . . . and wait. If necessary repeat step 7.
PS. I did not change key configuration, if you wand to do so you need java which is a pain to install in wine, so just learn the default keymapping.