Unfortunately I have the same setup as you and I pull much heavier than that, one way. My trailer weight usually doesn't run under 23K too often. I do run in 6th gear a lot, but I don't "lug" it. I've gotten better at downshifting into 5th.
I do regular oil changes. I used to change at 30K or so, but the oil comes out so clean I'm stretching that to 40K.
What can all be seen thru the pto holes. I could pull the fastcooler off next time and look, but I wouldn't know what I'm looking at.
Hindsight being 20/20 I screwed up getting the 4. 10's again, my '01 had the same setup. I'm kinda waiting for rear-end troubles so I can do a swap. Until something goes wrong with the rear end, it really doesn't pay to swap a 4x4.
I suppose I could just trade for a new CC auto, but where's the fun in that?