Note: this is not me saying "put this into different watch order" i'm just saying that those episodes in "specials" (of which most of them are NOT specials) should follow the absolute season release order and not be stuffed into specials, where it makes zero sense and is also against the TMDB guidelines. I originally wanted to do that, but then noticed the "Ended" marker

I think the perspective that whoever locked these episodes on TMDB takes is "if it wasn't on TV or aired not with the other episodes, it's a special". When proposing this change there need to be specifics like, "what about Tsubasa Cat 3-5?", "should Owarimonogatari be split up and in what order?", and "should Kizumonogatari 1-3 be omitted while determinging season numbers?". Changing the seasons requires changing the season images and may cause weird changes with databases that have had seasons in this order for a long time, and can cause people with Plex and Kodi servers to have incorrect episode numbers all of a sudden, which makes moderators less likely to make changes like this. If you can find somewhere that says officially what stories are in what season, that would be the best thing.

The guidelines for OVA/ONA are clear. As it was said before, if you want a different order you can use an episode group.