Hi Harmoniker,
This is a confusing situation, and I too would welcome any help in understanding what's going on. Here is a thread from a while ago devoted to changes in how iTunes uses the Work and Grouping tags:
Empty grouping tag for some but not all MP3 files
And I found this document out on the web, though it dates from iTunes v.12.5:
https://2manyrobots.com/YateResources/InAppHelp/English.lproj/pgs/iTunesGrouping .html
I use the Grouping field extensively. It seems (in v.12.7.5) that Grouping tag data is being written somewhere, because when I test by deleting a file from my library and then importing it again, all my eccentric tagging is still in place. But reports from users like yourself make me nervous.