Can you drive to the top of the pass and then turn around and return to Hwy 550 in a regular pick up truck. I've seen vids of the section from the Stairsteps into Telluride and I know my truck is no...
Cinnamon Pass is do-able in a regular p/u if you take it slow and the view is exceptional. 4WD makes it easier tho. We did it this last summer in our truck. I heard Black Bear is much more difficult but I'm not a local so my info may be off. I have a book on the passes but I'll have to see if I can find it. I don't think I'd try it this time of year tho.