I would just put in the 5.29's now, and be done with it! Especially, if you plan on going to 37's anyway! The 5.29's will make it easier to turn the boggers, since they are a heavy ass tire to begin with! I plan on running 4.88's only because I don't plan on going higher than a 35". And I (will) DD my rig too!
5.29 gears you will loose alot of top end on the hwy! 4.88 will still give ya decent hwy speed! This is why I'm gonna run 2 sets of tires. A light hwy set, that's good for on and off road, so I get good mpg. And an aggressive set for mainly off-road or winter time!