I get what your saying. Unfortunately as far as I can gather, there is no way to add anything to context menus from an script addon (other than plugins adding to their own file/directory list context menus). I believe a metadata scraper could be written that could show this sort of information when you click TV Show Information, but as you can only have one scraper active for each type of media that would essentially block usage of a normal scraper. I haven't done any work with the scraper interface. There may be some possibilities that I don't know about. I'll look into it. Hopefully XBMC will add some sort of addon interface that can create context menus. It would be nice if I could tell XBMC to add "Next Airing" to a TV show folder's context menu and have it pass my script the show name for example.
I'm kinda thinking out loud here
I'm glad you enjoy the script. I'll see what I can do on both #1 and #2 and post back here what I find out.
(btw as for the 'look' of the interface, I basically stole it from the Gmail Checker addon and modified it a little.

This was my first non-plugin script I have written for XBMC and needed to use something while I was learning)
ruuk