If you are going to run Holy Cross, you might as well run Red Cone Pass and Webster Pass. They are not far from Holy Cross. I liked Red Cone and Webster Pass. It is a big loop. The views and sights are great and the trail is technical enough to be entertaining.
Some of my favorite pics from Red Cone and Webster Pass
WE finished it in the dark. In this picture you can see the elevation change in less than a 1/4 mile.
My Jeep will leave NC in May, early June and won't be back until about October.
The Moab, Ouray, Holy Cross portion of the trip is right at 2 weeks.
That's leaving NC on July 20 and returning on Aug 4.
My Jeep will be in a storage unit in Missouri, but @UNC Rubicon will start his drive to get out there on the 20th. I'll likely be riding with him out there, but those logistics haven't been discussed yet.