yellowhair: Yes! Milk it as much as u want.
I no longer bother increasing scouting. But when I did, as I approached an ambush, if someone get's a scouting award, I would save the game. Then u take about 5 steps back, and 5 steps forward. If the scouting award happens again, save the game and redo the same thing. if it doesn't happen, reload, take 5 steps back, and 5 steps forward again.
So once u find that sweet spot, keep working it.
I use assessment in combat from time to time, but as it, and scouting, don't contribute much to combat, I no longer put any effort into increasing those skills.
By the way, it might be 5 or 7 steps, so just save it, and play with it a little bit to see how many steps are required.
I believe scouting does give you first move in combat if you detect an ambush which is important if you go up against multiple spellcasters.
Do save often since there is no autosave, because if your group is frozen and dies, the game is over.