How can you sync videos from Youtube to your iPad for offline viewing automatically? I'd like an application like Readability for iPad, that will download and cache videos on the iPad for offline viewing whenever it syncs with the Internet.

A qualifying application would let you do the following:


Flag a video for later viewing with a Google Chrome extension
Avoid having to use iTunes at all
Automatically download all new videos wirelessly to the iPad whenever the iPad app syncs (just like Readability)


Is there anything out there that's close?

It could be desktop software or a web application, it doesn't matter.
Watchlater does just that. Click a bookmarklet to add a video to the queue, and when you open the app, it will cache the videos in the queue.