Custom and importable lists with played, not played tracking

I would really like to do playlists for items to set a chronological universe play order.

Example: all Marvel TV Shows and movies in chron order, not release date order.

That and being able to know where I left off in said playlist.

Be even cooler if it was as easy as import list auto adds content to imported list even if some are missing. I had also noticed playlists remove items when replaced so have to re-add and shuffle the lists again.

You should already be able to sort items in a playlist to your liking (e.g. chronologically).
There’s been a number of suggestions discussing options to import playlists or create playlists based on files, e.g. Option to use existing m3u for playlist feature

There’s an existing feature suggestion discussing an option to store the progress inside a playlist and being able to resume from where you left off. → Playlists - Remember position for subsequent resume

Plex drops items from a playlist that have been removed/deleted from Plex. If you replace a file, make sure to add the new file before deleting the old one – this way, Plex will link the new file to the existing library item and you won’t loose manual edits or playlist assignments.

yeah automation can sometimes cause the gap… or just a bad file so gone for 15min or so is enough to make it drop.

If that can happen in your setup, disable Settings > [Server Name] > Library > Empty trash automatically after every scan

2022 clean-up: duplicate(s), available configuration options (implemented)