Stony is pretty rough on the west side of the divide, I banged up my skids pretty good on it. It''s definitely easier going from Silverton towards Creede but it's really nice at the top. I was there last week and Pole Creek wasn't a problem at all.
I probably wouldn't pull a trailer on Cinnamon Pass from Lake City towards Silverton. I think the last switchback on the actual pass, on the Silverton side may get a little sketchy, depending on your clearance as it's pretty tight with about a 2' camber. I'm fairly certain that you can hop off of Cinnamon around American Basin and not go over the Pass, which get's you about 75 of the way along Cinnamon. Just watch out for the side by sides. They're EVERYWHERE along Cinnamon pass.
Oh and remember, that whole area is under a burn ban right now. Check with the different fire districts to see what allowed and what's not. Right now the whole area bans any kind of open flame.