On a few trails around here, the 2.71 or lower is good for some sections but then it gets easy for a while and you end up shifting higher and higher all the way to 4h or 5th, then decide it's better not to rev it too much, so you shift to high range just before you need low range again. I think this is a fairly common scenario for an expedition vehicle. It gets to be a pain with 2.71:1, can only imagine how it could get with 5:1. I used to think gearing overlap was a waste (almost decided on a 5:1, actually ordered a 4.3:1 but was lucky the order got botched so had a chance to get the 4 speed) but it really makes the Jeep more pleasant to drive when the trail difficulty is changing along the way. Doubler is the way to go, you will be happier in the long run.
The way I see it: 5:1, cheaper, very good but could have some regrets; 4 speed, more expense up front, but most versatility and no regrets.