Anyone remember the Darknet Diaries episodes about a bunch of white hats from the Netherlands who managed to guess Trump's Twitter password twice? I think this was after he started campaigning for what would be his presidency, and then again a few years later.
Here's the first of the two episodes: Darknet Diaries: 87: Guild of the Grumpy Old Hackers mp3
Installing the Jellyfin add on into kodi takes a few minutes. Nothing much to consider, just try it and see if that changes anything.
I have a similar setup (rpi with OSMC, media hosted on file server) and prefer using Jellyfin as the source for all clients, as it keeps track of watched status across everything. It's not perfect, but better than without Jellyfin.