I have done it with my 99 Wrangler, 2 1/2 lift, 32s, 3.73s, (at the time), had to be winched through French Creek, there are winch anchors there, and in another spot closer to the top.
Guy I was with did it in his 85 CJ 7, 4.56s, 32s, and lockers, and he did not have to winch through any area on the trail.
Both of us went up and back with no vehicle damage. I think 32s, winch or lockers, or both would be the minimum to try Holy Cross with. 35s, lower gearing, lockers, would be better, but it can be done without having a max modified Wrangler.
I think the damage you may incur is directly related to how much thought you put into getting through the obstacles on the trail.