There aren't a lot of 8spds out yet with a lot of towing miles which is probably why OP isn't getting a lot of direct responses. From what I've read people are VERY happy with the combo, especially compared to the 6spd tranny. It really has upped the range that I'd consider using a gasser. 14K? That's definitely getting up there.
I recognize a lot of names on this thread that I'm sure know this but just to clarify for people that don't know - the 6spd tranny is a well known disaster. A total waste of a good engine. The gear ratios are borrowed from the diesel truck tranny and are just not good with gas. Someone mentioned stuck going 35mph - this is the crux of the problem. The 1-2 gap is a mile and the truck can't hold 2nd. Other problems are with shifting behavior - skipping 3rd, slamming into gears, holding gears to long, etc, etc. From what I've read, all of this is better with the new 8spd.
My $.02 for OP - I'd go up to 14K if I didn't plan to tow full time and/or in the hills a lot. I suppose you could also go 8spd and re-gear to a 4.56 or 4.88. Re-gearing with the old 6spd was a hot topic to try to help with the tranny problems. I'd have to think the new 8spd with higher numerical gears would be a beast. After all, 14K trailer and 8K truck (assuming some things in the truck) = 22K. That's nothing compared to what some of the gas engines are moving around in the class A coaches. Of course, the largest F53 chassis that the class A units are running on have gearing up over 5:1 (I'm thinking 5.13?).