We can't crawl while carrying a battering ram. Unless we're planning to discard it, it's no use. That, and the fact that we're more likely to be hit since the enemies get more attack rolls at us.
The problem, as I see it, is that any plan that reduces our movement means more incoming arrows. Even if the penalties are stacked (cover, concealment, possibly long range, but I doubt so), they will hit now and then. Add to that that a failed endurance test for those carrying the shield means no cover for that round. The fewer rounds we have to move, the possibilities of failed cover. Thus, I suggest we just move as fast as we can, double moves all the time.
Fortune doesn't need hands to attack, but she still needs standard actions, so she wouldn't be able to keep up with you if she did. It is, however, a possibility for her to lag a bit behind the others and fire off dishearten every round. It has two purposes. First, the -2 to hit will make it less likely that we'll be hit. Second, if they're not very tough, I might be able to kill a few. Even if they are replaced quickly, it will probably give us less incoming fire for the one round it takes to replace them. She does expose herself to more fire that way (no cover from the tower shields), but she's most likely a less priority target than those carrying an obvious battering ram.
When you get to the gate, you'll most likely need to discard the shields anyway. You need the strongest one (Gruunk) to work the ram.
Summarizing that plan, it'd work something like this:
- Tarner and Gruunk carry tower shields, as they are the only two that are trained in Endurance. Double move each round.
- Nurse and Eduardo carry the battering ram. Double move each round.
- Fortune provides "cover fire". Move and standard each round.
An alternate plan would be to have Nurse disguise as a drow and draw fire by pretending to be a commander. The main disadvantage with that plan is that he's (or she's?) not extremely tough, and might simply go down from the fire.
Fortune also has two flasks of oil. We might be able to do something by lighting the oil, but I have no specific plan yet that would grant us an edge.
I vote for the straight-forward plan myself.