To make the squash, preheat oven to 425 degrees F. Toss acorn squash wedges with olive oil, chili powder, and sea salt, and arrange on a large baking sheet. Roast 30 minutes, turning once halfway through. (Squash should be cooked enough to just accept the tines of a fork – if overcooked, they may fall apart on the grill.) If making squash ahead, cool completely and then refrigerate; or on the day-of, just set aside until they're needed.
45 minutes before serving, prepare a hot grill.
*If using un-frenched rib chops (about 1/4 pound each), reduce cook time to 2 - 3 minutes per side.
**Timelines can be tough on Thanksgiving, and owing to a nice amount of fat, shoulder chops will keep 20 minutes in a 200 degree F oven if things aren't going as planned.