We have run a lot of the trails in that area including Black Bear Pass. Black Bear is not that difficult technically, but there is no room for error since you are near the edge on some 3 point turns. There are also some "steps" that are scary because of the loose rock. I saw the right rear wheel of a Liberty about a foot off the ground there.
I just confirmed my reservations today for 21 or 22 June to June 30. I will be at Silver Summit RV Park in Silverton but they are full up. I will have to drycamp on the 21 thru 23 since they can't get me into the RV park until the 24th. In other words, the town looks pretty busy during that time. There are several events during that period that take up a lot of space.
I would like to run the Engineer Pass/Cinammon Pass (commonly known as the Alpine Loop). Ran it last year with 1 other TJ and had a good time. Pretty bumpy in the beginning but not real difficult.
1 of the most scenic rides would be California Pass/Hurricane Pass/Picayne. It is an easy trail but the scenery is spectacular and there is an old mill on Picayne that has self guided tours so you can see how gold ore was processed. You may see this trail called "Picayune Gulch" bit it's proper name is Picayne Gulch.
http://ouraycolorado.us/index.php?page=jeeping has some good trail information.
The only trail we have not tackled yet is Poughkeepsie Gulch and it is the highest rated trail in the area. From what I have heard it is not advisable without some good ground clearance and a winch.