When I have a multi-episode file.
Pride_and_Prejudice - S01E01-E04.mkv
It obviously can’t tell where episodes 2,3, and 4 start and end, so I have to watch the whole show every time.
Instead, make the file-naming
Pride_and_Prejudice - S01E01Ch1-E02Ch02-E03Ch03-E04Ch04.mkv
When you parse the Episode, you grab the Chapter that goes with it, and jump to that point in the file. Easy peasy.
If you want to get fancy, you could even add the end-chapter, but the parsing might get complicated.
If chapters are too hard, you could just use the play-time, in whatever format.
That might be fine for 4 parts, but what if there are more. 
My OS can have 255 character filenames.
That’s a lot of episode pointers per file.
It’s an interesting idea, but Plex already supports chapters for TV episode, so this would get confusing.
If you already know where the breakpoints for the episodes are, why not just split the files and not worry about having to deal with this.
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Sometimes TVdb will have multi-part episodes for shows that aren’t actually multiple episodes. Particularly for ones that are 2 or 4 parts or shorter stories that aired as Episode 1 but was split into Episode 1 & Episode 2 but they are intended to be a single episode. This usually happens when a DVD version has the parts split differently. There is still only a single opening credits at the beginning of Episode 1 & a single End credits at the end of Episode 2. I don’t want those to be separate files. But it would be nice to be able to start the 2nd story if I wanted to & more importantly not have it play episodes 1&2 for episode 1, then play episodes 1&2 again for episode 2. What brought me here today is a special feature that is a collection of 60 shorts, 20-60 seconds each.
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Plex already recognizes that this file is being handled differently because it shows it as 72 episodes (each week there was a 2-3 minute compilation episode of that week’s shorts so there’s actually 72 entries in TVdb.
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It shouldn’t be hard to have it, when it recognizes a multi-episodes-split-across-files entry, add a field in the Edit Screen to [Start at __:__:__] & have it start the file at that marker when you click that episode but just keep playing & when you’ve passed the start of the next marker mark the previous episode as played. It’d be nice to also have the ability to set an [Ends At __:__:__] field too, but I can understand there being potential issues & it doesn’t really add anything except maybe for play progress markers.
But splitting is always, no matter what, an imperfect thing. If you want to split wherever you want you’ll probably have to reencode, & loose some quality. If you want to not reencode you have to stick to index frames or create issues with the files & even if Plex will play them without issue, other players will not
