You'll be happy to know that the answers to both your questions can be accessed via the links on the DiplomaticCorp home page.

1) Does Youngstown ever get played here? Yes. Twice to date (DC057 & DC154). You can see those games in the Hall of Games.

2) Are there good color / downloadable maps? Yes. If you follow the Variants link and scroll all the way to the bottom, you can link to the DipWiki for Youngstown. At the top of the DipWiki page, there'll be a boring old black and white map. But further down is a color map.
Returning to the variants page, there is also a link marked 'RP', which allows you to download the RealPolitik files for Youngstown (RealPolitik is a Diplomacy adjudication software which I favor).

Now, for the reeeeeaaaaal question: does anybody fancy a game of Youngstown? I've always been interested but also a little scared off by those off-board boxes. I could be tempted to play (or GM... but I think I'd rather play for a change).

Adam