"I have a 4 hour flight next week, grab the Top Gear specials and send them to my iPad". Or a step better, an LLM looks ahead to your calendar and just figures it out.

As far as I know nothing exists today with enough context into each of the elements required to make this relatively simple idea work.

Imagine if the LLM involved here knew the iPad you were talking about, the current free space, it's resolution, and any other constraints and just handled the complexities - including offline transfer and encoding of the files to a suitable file size for the target device? Synced watch status and all the rest of it via Jellyfin would be neat.

After all... how hard can it be?

I suppose you could string together a bunch of this stuff together with n8n and ffmpeg perhaps. Anywho, I could see this being the future of software both commercially and for self-hosters.