1. leveling to 39 on Lord takes a few hrs /played if u have help which we provide. There are no heirlooms on Lord so no need to level a main. If u want to twink on Icecrown u need heirlooms so that requires you to also level a main to 80, which takes much longer than even leveling to 39 on your own on Lord.
2. See above, and, because the high rates there will be a severe shortage of the worlddrop boe's, while Lord with its much larger pop and x1 rates has a lot of them all. I'm referring to not only the rare/epic boe's, but also the green suffixes.
We'll see just have to see how it plays out. I logged in to Icecrown a few times but didnt see anyone on... maybe I was just unlucky :P