It's been several years since I've made Black Bear - always in a Jeep making them very maneuverable. I love that view coming down into Telluride. If you haven't, you should try Imogene. Not as technical but has some pretty nice scenery and road situations....and, you can always leave a note at the mailbox at the top...
Unlike Black Bear, you can start at either the Ouray or Telluride end.