I'm thinking that Tommy would probably be best suited either for the noble district or the Flowerlands, given his spec as a negotiator. I think as far as the noble district is concerned, he would see the guards as being potentially better people to talk to since they're not necessarily too high up on the totem pole, but he'd be down for engaging the young man on his own. As for the Flowerlands, Doro or the old man seem like they'd be good choices, but Tommy would probably be more keen on Doro.

If you just wanna hang though, Tommy will be at the spring festival. During the ambush, Tommy could but won't be helping with subduing the ambushers. In fact, more than anything else, he'll probably be observing the conflict from a reasonably safe distance/somewhere concealed. The morning after, he will likely make more direct efforts to clean up the mess to try and get a better read on the situation and ingratiate himself.

Bounty-wise, I'm down for any of the main bounties, but not so much the special bounties this time around. In particular, let's get sloshed on sake or tracking down those boxes of tea! :]b