Maybe 5 or 10 low level battle challenges daily for Annabelle and Dirty Matty that don't scale up after each battle. You would get a guaranteed cheap-ish item from Rathskeller Inn on win, a small spot of sP (about 200-500), and a chance at a pirate item that skews towards the current year's batch. Something doable by people who don't battle, but might encourage them to train up, if only a bit, and would only require some cheap weapons to do. The flavor text could be that Annabelle needs to blow off some steam and Matty needs to sober up. No challenger loot- you need to do proper battles with scaling and reward limits for those.

Going by what Amber said in another topic, it won't be possible to anything major for item distribution this year. All I can think of for this year (which mightn't be as easy as I think) is changing Carl's quests so he only gives out new items for the rest of the holiday.