For now with the cart Jonathan will take the lead, in a scouting position. I think that Tomas should be the lead of the acutal group. Anntreen and the children should be in the center on the cart, and Krusten should take reargaurd.
Jon will keep my everything but my weapons, armor, clothes, and waterskin in the cart as well, considering he will only need his weapons, armor, and waterskin during the day
That's fine, but if you are in the woods behind the party acting as rearguard, that would probably be better than a person just walking behind the group.
In that case, Tomas will take the rear, albeit grumbling about it, but realising it's an equally vital position.
So Jon will be a bit ahead to scout, how far do you think he would be?