Update on current position:
We have resolved known issues where the problems were in boost or Plex Media Server
In PMS 1.32.4 we brought back the use of the boost libraries on Windows - in 1.32.3 they were bypassed whilst the issues were investigated.
There remains now one problem area relating to symlinks to softmounted drives by virtualbox. This was looked into as a boost issue here directory_iterator does not work for mounted volumes (1.80) · Issue #261 · boostorg/filesystem · GitHub and subsequently identified as a suspected virtualbox problem which is now covered by this support ticket #21351 (GetFileInformationByHandleExfor VBoxSharedFolderFS works incorrectly) – Oracle VM VirtualBox - anyone with this setup, please progress with virtualbox using this linked support ticket