kevh, I generally agree with your assessments of the roads. And yes, now that I think about it, Holy Cross is better suited to vehicles with lockers and winches and 33s (I haven't been up there in quite awhile). I was just looking for beautiful, high elevation roads to get away from the heat. Bill Moore Lake (up from Empire) or Red Cone Pass were going to be my picks, although Red Cone pass gets much higher (12,800 ft at the pass). Wheeler Lake trail is one of my favorite roads, and as you pointed out there are multiple lines to bypass some of the toughest stuff, but I was hoping for more vehicles (3-4) to do that trail. Red Cone pass is generally a pretty easy trail, with the exception of one very steep, very loose downhill spot off the pass. Otherwise, I think a stock Libby could probably do it. Skyjump, it's no problem if you'd like to join up with the msv/coney creek group. I'm sure other runs will come up soon...like next weekend!
Oh, here's a fun site with pretty good trail reviews and lots of pics:
http://www.traildamage.com/index.php