UniversalMediaServer VS Emby

DLNAmpvRenderer UMS

You can give a try to apps like Universal Media Server, they usually do the trick on Windows.

Download and Install Universal Media Server: Go to the official website (https://www.universalmediaserver.com/) and download the latest version of Universal Media Server (UMS) for Windows. Install the application by following the on-screen instructions.

I've never used a Jellyfin media server. I've usually just used Universal Media Server and it does read/stream/transcode iso files on the fly and stream them to any DLNA UPnP device on your network

You could try streaming to your PS3 via https://www.universalmediaserver.com/

After you have your SBS video, you then have a few different choices on how you want to play it on your Quest. You can play it on your computer with VLC and connect to your computer with BigScreen remote desktop in SBS mode (not the best because the controls for pause, rewind, ff, are difficult to hit this way), you can buy Skybox and play it off of an SMB share, you can buy Virtual Desktop and stream it from your PC, or you can setup a DLNA server such as Plex or Universal Media Server but not Window's builtin DLNA server nor Jellyfin and play it in BigScreen, Skybox, MoonVR, or any of the other video players that support SBS video played from a DLNA server.

Also, the newest version of Universal Media Server has a new feature that will do on-the-fly conversions of 2D content to 3D. I haven't tried it yet, but do have a guide on how to set it up for Quest 2 saved somewhere. Ah, found it. Not sure how that compares quality wise to a ripped 3D Blu-Ray.

I used to use Plex until I found Emby. I find Emby easier to use and it does the same thing. Just putting this here as a fourth option for OP. :)

Media Server: EMBY

I use https://emby.media along with private trackers and Usenet.

You can find it here! I have both installed, but I generally keep EMBY turned off until I want to play around with it. You can have both running at once and both accessing the same folders. You can check it out for free.

Emby: Offers premium features with some behind a membership.

I went with Emby, personally. Plex, Jellyfin, etc are all good choices too! :)

For clarity: Emby is still mostly open source (the source code is right here: https://github.com/MediaBrowser/Emby). Emby started incorporating closed source plugins that you only get with the paid version of Emby in order to try and get revenue.

I used Plex until I found Emby, which is far easier to set up and works very well with all my media.