This is a nice idea, but not something we'll be including in Jetpack itself. You would need some way of adding meta data of some sort to images, and some way of modifying the Tiled Galleries output to include this meta data. To modify the Tiled Galleries, you'd have to modify the plugin files themselves, as there's no way to filter the output of the Tiled Galleries. I suggest asking in your local WordPress community for a developer who can help you build this functionality, if you're not able to do so yourself, but since you'l be modifying the plugin files, your changes would be overwritten on every plugin update and would need to be reimplemented, which isn't ideal for a client's site, I would think.
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