My user opinion about PlayOnLinux/PlayOnMac, mid 2019.
POL/POM was a active project until ~2015. Now (mid 2019), it lack of active developpers (the few active are busy on POL v5). Lots of installation scripts, POL/POM functions (most of them translated from Winetricks) are lacking updates, and/or are broken.
My advice to the newcomers to POL/POM :
If you want to run Windows applications (not listed in our 'Supported Software') on Linux/Mac by using Wine :
1. POL/POM v4 can still be the best choice.
2. The harder way (I mean for a command line newbie) is to use Wine + Winecfg + winetricks.
If you want to run Windows games (not listed in our 'Supported Software') on Linux/Mac by using Wine :
1. With the updates of Wine (ie: v4), most of pre-2015 games can run without any hacks, just with Wine. Many of my recent scripts in POL/POM for some games just do this.
2. If your game can't work with POL/POM v4 (perhaps because of lacking POL functions matching to Winetricks), look at Lutris.net until POL/POM v5 has a beta release version.
If you need a professionnal support (for applications and games), look at CrossOver project.