Your duck sounds divine. I love the pomegranate. We just had duck last week with a wild grape sauce, you're reminding me of it, it was clear, not cream, might be worth considering a clear pomegranate sauce? I also like the sound of your leek soup, especially as a clear soup thinking French Onion as you say, it's making me crave Gruyere!
I had some thoughts on the butternut ravioli, or the butternut risotto as suggested. (I also sometimes do a fairly light butternut squash Gnocchi, which always seem to get raves). But then yesterday, I was tasting a few different types of organic heirloom squash, roasted. Ooh la la, were they ever good, some quite chestnutty in flavor. Then I thought what about just the right variety and quality of squash roasted (or grilled). I want your duck to take center stage, a nice roasted caremelized squash goes nicely with the pom too. I was thinking Braised (or grilled) Belgian Endive as a possibility for the veg (easy to plate up and fairly non-picky, a subtle taste against the duck and pomegranate). I used to make a braised endive with a little Framboise, maybe you don't want something like that, but it made me think it would be a nice complement to the Pom. I'm thinking easy to plate up, easy to deliver hot, and let the duck speak. Asparagus to me said spring, if you want that shape but in "the fall line", you could go with Broccoli di Rabe/Rapini, but you'll have to tell me if you want bitter green with the other flavors, maybe.
OOH, I just read roasted parsnips. There's a nice recipe in one of the Silver Palate books which has roasted parsnips, kumquats, pears, etc. I'm trying to remember all the ingredients, I adapted from it as it was a little sweet. A combination like that could be worth considering duck, the kumquats sort of evocative of a l'orange. You don't need that many kumquats to keep it in your budget.
Just some thoughts from a pastry type thinking out loud... what do I know!
The only other thing to me that didn't say fall was fresh tomato (to me that's summer), and are tomatoes really delicious at this time of year where you are? I was thinking switch fresh tomato to roasted tomato for more of a warm fall flair and more concentrated flavor. Or half dried in a very low convection oven are very delicious, a little of the sundried taste, a little tang.
LOL too many cooks spoil the broth!