In my opinion, this is a rather complex and not entirely obvious mechanic. To acquire loot, you need to: 1) sneak up to the one who has the loot bag, and take it; 2) run across rough terrain to the battle; 3) pick up the loot; 4) give the loot bag back to the "dad" so he can continue along the road; 5) take the loot bag from "dad" at the end of the day. In total, the "sneak" unit doesn't have enough movement points for this :(
Could you provide more details on how to calculate the army's trajectory?
These are typical logistics problems (in the business sense, not in the Heroes sense).
To see real-life examples, I recommend watching game streams through Mikogo; it might become clearer. You can find the stream numbers in the VT chat or in the corresponding thread in the online third game section.