I'm on 34s with 4.88s now and they are perfect for towing this Kimberly Kamper Kavavan around in mountains with head wind. I wouldn't go 5.29s with 35s or below unless you were towing something like a 27' airstream (god I love those).
I'm looking at doing stupid stuff, and the first thing I want to ensure is that I can set to a 5.29. Or i'm gonna take an 8 speed and fit it to my 2011 and then my 4.88s will be fine.
Separate of that, and this is how I feel about it, regearing isn't for the low end. It's for the high end. I mean high ground speed with low RPMs. The cruise range, when your power output is low, but you are pushing a ton of wind out of the way and trying to pull heavy things. That's where the constant down shifting comes from. 5.7L has plenty of power for the acceleration, 200 has plenty of gearing for rock crawling. But the highway is where it suffers in my opinion when heavily modified, not at all when stock or mildly built.
And the 8 speeds will run about 100 RPMs lower than the 6 speeds. So for me, I like the stock gearing setup better on the 6 speeds.
The only reason i'm looking at 5.29s is because i'm figuring up the plans for much larger tires.