i suggest running the 5:29's from what i've read.
if it is a trail only rig then running dual cases with the gears you have would work.
if you are driving this truck daily and towing with it definatley run the 5:29's
runing too high of gears not only causes the problem of too high gearing for crawling it also makes your trans. gear ratio too wide. so you'll be screaming the motor in 2nd and then shift to third and it boggs.
this is also hard on your trans. and motor. the lower gearing wil shorten the transmission ratio. so then you won't be hunting for a second and a half gear.
another thing, is that with the 5:29 gears, the pinion gear is real tiny. so they don't last as long as the 4:88's.
it's kind of a choose you poison choice. but from what you have said it sounds like the 5:29's would be the best road for you.