That's a good itinerary Mike.
Even 4wd stockers should be able to do Poughkeepsie Gulch except for that last obstacle. As long as some capable vehicles are in front to strap others up, you should do fine.
As for Black Bear, there is an alternate for those who don't want to do it. Here's a direct paste from our Colors Run 2000 itinerary and it worked great:
"Saturday - meet at 8:00, leave by 8:30.
Group One runs Ophir Pass (Trail #5) to Telluride. Meanwhile, Group Two tackles Black Bear Pass to Telluride. Then both groups meet in Telluride and take Imogene Pass back to Ouray. Telluride will have its Main St. blocked off that day for its annual Film Festival but we will be able to go around side streets through town."
That film festival may be going on again during the same weekend, so someone may want to check that out.
Group One got to Telluride before our group did and watched us go down the switchbacks from the town below (bring binoculars) and preceeded us on Imogene, with our group catching up and the whole group ended up together on Imogene. Heath and others may want to do the same thing. However, IMO I agree with what Mike said - Black Bear is not that dangerous. Yeah it's scary but if you take your time and drive carefully you'll enjoy the thrill of it. Just make sure your vehicle is in top shape with good brakes/etc but you should be doing that anyway before any run, right?
Someone may want to move this thread to the main Trail Runs forum. A lot of people from outside Colorado may want to join, but not be looking at this thread. You guys have a great time!