Day 1 sounds awesome. Dare I say... Legendary!?
Silver Creek will be a great starting course. I'd suggest skipping the 2 holes on the south side of the entrance road, and use that 15 minutes to chill on the bench at 14
I'd cruise up to Winter Park second. Sorry Superberry, but I'm gonna suggest skipping the holes after 15 to make time for S.R. But definitely play the lettered holes!
If you can finish at the Ridge by 3:30-4, there will hopefully be enough daylight to get through Standing Rocks. That would be my big concern. It's 95% under canopy. If the ETA is after 6, I'd consider hitting up O'Hauser instead. It's 5 minutes offa 10, and you'd get up to Sandy point by a decent hour.
Good luck fellas