I recently read on a GT list serv somewhere about a parent that had a child memorize a multiplaction table every week for 12 weeks. If they could recite it cold on Friday, they would go to a movie or something like that. I think rewards shouldn't be overused, but when it comes to something like this, it may be useful! This is one of the first things I was thinking of working on with my DS if we homeschool. He sounds like he's exactly where your DS is in terms of math fact recall. And I totally understand about needing him to buy into an idea! I think this is part of the deal that makes a regular school so hard for these guys, isn't it?
I also think Grin has a great point about being developmentally ready for certain things. We had the exact same experience with learning to read an analog clock with DS. Only recently mastered skill. We also don't own a functional analog clock either, so I suppose that didn't help at all.