I read through your post twice. It seems like a lot of work but I imagine once you do it a few times you get the hang of it. I would be worried about having to capture the save state twice.
I am toying with the idea of doing things in preseason to start, so I can at least get 5-6 guys committed to something without the harsh time constraints. You get 3-4 months to play your games, you can play them in any order, as long as you play all of them by the deadline. Problem with that is no stats/injuries but at least it counts towards something.