Does your motherboard have a boot menu option?
I haven’t done 2 Linux installs in this way, but for Linux / Windows I don’t really “dual boot”. I have two separate drives, with two separate installations. I can boot into either one, even if the other drive is missing.
I did each install with all of the the other drives removed from the machine to keep things clean. Then I can just select whichever drive I want to boot into from the motherboards / UEFI boot menu.
The only downside to this is that I do have to select a default boot drive, so if I’m not paying attention, Windows update will reboot into the Linux installation since it’s the default drive.









There’s no automated way to handle it, but you can probably speed it up a bit with a few tools.
Generally once you find the first episode of the disk, the rest will be named numerically after it, so maybe the special features or FBI warning or other misc things are the first track or two (starting at 0), or it could be the first episode, but once you find that one the rest will usually be named in order (t0_01, t0_02, etc).
In Windows, I used a tool called Bulk Rename Utility (https://www.bulkrenameutility.co.uk/) when I did this in the past. Once you figure out how to use it, you can rename all the files at once in the folder in a format (show_s1_e1 or other supported format pretty quickly. It won’t be automatic, but will be way faster than renaming them by hand.
I usually use TheTVDb to do the naming, that way the shows can be found / indexed easily.
The only thing that you’ll have to keep in mind for show rips, is that many times the DVD order isn’t aired order, and they may not match the order on TheTVDb, or other source, so you may have to rename them in Aired order occasionally, or change the settings for Jellyfin: https://forum.jellyfin.org/t-resolved-dvd-order-instead-of-aired-order