>>116488This bothered me a lot at first to but I've managed to get around it. You can list episodes in "absolute order" to get around needing to break things into seasons. For OVAs/movies and related specials you can maintain a "specials" directory within the main directly and rename those as needed (usually just have to tag them with something like S00E01).
There are bots that claim to automate the renaming but ime they all suck. They don't have proper interfaces either you'd expected to interact with them through a web browser. I gave up on all of that and just started manually renaming things as needed.
This morning I added about 10 new episodes from currently airing series. Out of all of those I only needed to manually rename one file. Most people are getting better about conforming to the way these servers expect files to be named. Even "S3 - 08" works as well as "S03E08". Although I agree it sucks for anyone that wants the old-style file names where episodes are numbered by total number of episodes.
What I do is keep absolute orders for old series or series with a hundreds of episodes (e.g. Bleach, One Piece) and use seasons for seasonal stuff airing now or things released with PleX-style file names.
There is nothing requiring you to keep everything related to one series in the same area either. For example, whatever that new series of Bleach is called is separate from the original series on our server. I do the same thing with a lot of movies.
Then there are series like pic related. Where manually renaming and properly ordering things would be a huge pain in the ass. In those cases I keep them in separate listings and manually re-order them using "sort order titles". In the case of pic related they are mostly in the intended watch-order and I supply a playlist in the correct watch order for anyone interested in watching them for the first time. Not that it helps me. I explained the playlist/series to someone multiple times. They still randomly picked up one of the OVAs and were confused about everything going on. At that point I showed them the playlist for like the 10th time and they promptly dropped the series to go watch something else after seeing how many days it would take to get through everything.
All that said I find this much better than the way I used to watch stuff because I can access the library from anywhere in the world as long as my home internet connection is up. It's very useful to only have to lug around a small set-top device instead of a laptop with data I've copied to the HDD before hand (or an external HDD). I keep all my music on the server as well. So my music library can go with me everywhere.