I could be a look-out. Poppy has a perception of +4, plus Natural Watchfulness which gives her double proficiency bonus to perception when in the Wilderness. In addition, I could also be a hunter since I do have Hunter of Beasts, but that's only for tracking creatures (double proficiency bonus when making Wisdom (Survival) ability tests). And...I also have proficiency in pure Hobbity Stealth...lol.
Also, I realize now I never wrote these down:
Known Lands: Mirkwood, Middle Vales (idk if they count as one or two since there's an east and west), Long Marshes