Bottles was having the same issue. I was attempting to install SimTower off the CD copy I have and they all were having issues running. I believe it’s a permissions issue that I could figure out, but not sure. After spending hours i went down the distro route and it worked perfectly the first time. Was able to run the installation for the game and launch it from wine.
I avoided transcoding by making sure to only host videos compatible with all clients. Also, I will spend the time to reencode codes that are too large for my taste. Which happens after a rip of uhd disks.
H265 with slow preset really works wonders for non-grainy film. AV1 is what you have to use when there is grain.
I would vote for running jellyfish off the NAS with powerful hardware Intel 8th Gen and up you should be fine. I personally don’t transcode video on my server only audio.
If I’m not sure about a video format working, I’ll manually re-encode the video with handbrake to h265 or av1. I also have used handbrake to create lower resolution copies of the same movies to reduce bandwidth needs when roaming on LTE.
Isn’t that what happened to the schools during COVID or something with one of the programs. I forget…