Thanks so much for your response!
Smart Collections
I agree, you can create smart collections for episodes. I tried it and saw it actually put those Specials after the episodes, unlike the normal “Season” view.
I don’t always buy anime I wanna watch either. Some I buy to watch with my kids when they’re a bit older, but not today. And this means I have to go to that smart collection to watch the show, or I might miss out on specials.
There’s also no way my kids are gonna set up smart collections at their age in their account. That’s even more work for me to do. I already have to name all the episodes and features and organize everything; I’d rather not have to spend even more time customizing Plex. I’m supposed to watch and enjoy media, not spend all my time organizing it.
TVDB is wrong in some cases 
If TVDB is really the source of truth here, I’d like to figure out how to update TVDB.
Here are some descriptions on OVAs from the One Punch Man disc:
A story set sometime between Mosquito Girl’s defeat and Genos showing up to Saitama’s apartment.
After the events of episode 4…
After the events of episode 7…
All of these show up separately in Specials and their “air date” is after Season 1. And after watching all the Specials for this series, I realized they should’ve been littered throughout the Season 1 episodes.
In this case, I’d say TVDB is wrong, but Plex doesn’t let me drag 'n drop episodes outside of Collections either, so I can’t fix it without fixing or adding to TVDB.
The Aired and DVD orders are correct, but they don’t match where these should chronologically go. I wish there was another sorting option for “Story Chronological”.
Movies mixed with shows
You said there’s a special case where movies can show up correctly right? Do you have a screenshot of that?
Other comments
I’m glad others are asking for support from AniDB and others. It would give me way more options. Even when using them, I’m still stuck to whatever TVDB does for sorting.
In general, I want to avoid doing custom stuff in Plex. I don’t mind making Collections for a series of movies. It helps thin my movies list too since I hide items in collections.
For shows, I could see making a collection from various seasons and movies, but it’s sub-par because there’s a watch-order I want to keep, and sometimes prequels are meant to be watched in that order. As you’re saying, a lot of this is on TVDB and others.
Custom Ordering
In the case TVDB doesn’t do it, I wanna be able to setup custom ordering in the same way I can reorder Collections. But this requires I have “Seasons: None”. That really depends on how I’m organizing things.
If I’m using American ordering (what you find on Western releases on disc), then I want Specials ordered inside of Seasons and ideally have that come from TVDB.
If I’m using Japanese ordering, then I want each Show to contain a single Season and for me to order Specials correctly in that Season. That also means movies would need to be counted as Movies, not Shows like they are today.
P.S. I removed that “as a developer” comment. You were completely right. Thanks for the help!
