I just installed PB2019 on a Windows 2016 server (64-bit) and migrated our application. No errors. Did the same last week on a Win10 desktop. Migrated the application there as well.
I noticed that I cannot regen any datawindow objects in the 2016 server installation, but the Win 10 installation is fine. The error is fairly useless in that it says 'Regeneration of library entry failed. Continue?'. Failed how/why? I suspect it has something to do with the database perhaps? In that regard, I am connected to Oracle and can select data with the database painter, so I don't think it's a profile issue. But it sure smells like something database-related.