Sadly, this is unlikely to happen.
I'll cut to the chase first, and say it literally cannot be done with an addon, as addons cannot interact with anything outside WoW.
From there, it's unlikely that anyone will ever implement it for vent, since vent is closed-source. That kind of interaction would involve either reversing the vent protocol and designing your own client, or reversing the client itself and designing an interface.
Not only that, but you have to recognize that with the quality of the transmissions, the myriad of voices at once, and all the different voices it would have to pick out and understand, most modern speech recognition algorithms aren't going to have a chance of providing anything useful in terms of output. Of course, I'm hardly up on the latest research, so maybe I'm out of date.
For the short term, as far as I can tell (after only a small amount of research) you really don't have any options, other than to try to keep him up to date through the chat frame. In the longer term, if you can build enough interest in something like that for an open source platform (e.g. Mumble) it might happen, but the technical obstacles make it much less likely.
I'm sorry I couldn't be of more help, and I wish you the best of luck!
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