Hmm...ok, new thought. What if Eldeth gets bumped to the back to cover tracks, and I aid Shuushar with navigating? As a scout Eldeth should be solid at covering tracks, and she won't need light back there since she's got darkvision.
I'll be up front anyway, and I've got +2 to survival. (I take it I can be a few paces ahead of Shuushar and still be aiding him just by memorizing terrain or whatever--the whole point of my being up there is to be the idiot who springs traps/takes the first arrow to the knee, so I don't want to be level with the little space cadet). Plus, the "Wanderer" feature of my background says I "have an excellent memory for maps and geography and can always recall the general layout of terrain, settlements, and other features around you." Hopefully that will help the roll a bit more.
Bertram could stay as front lookout, and you (Ezraen) and Sarith could be the rear lookouts (drow buds 4 ever!). Topsy could be dropped as a lookout and just forage.
How does this all sound?