Auto converting to itunes?

Hello all,

I'm getting ready to cut the cord. We were using a mac mini with Plex, and a plex server +TV shows, but my lovely wife got me an AppleTV for christmas.

Now I like it a lot. "It just works" as they say, but I was really enjoying my tv shows. I can use handbrake to convert them for iTunes, but its a manual process.

I'm not sure about jail breaking, since the system just works as it is.

Does anyone have a setup like this?