Well shoot.
So I'm not too far from a guard outpost, right? I manage to bob and weave and fall back to the outpost, thinking that the guard will help me out - after all, it's been a while since they've had a good bandit raid. I get there, and I hear "This should be good."
What.
"Oh, look, a fight."
Are you... kidding me?
So they're leaving little ol' me to fight off the bandits, with like, no combat training to speak of. Cute. Somehow... I managed to do it. Granted, I think I blew through a third of the stock of potions I had made, but hey, it's not like people in Whiterun need healing or anything like that, right guard guys? Nothing like wars or illnesses going around, nope, a perfectly healthy hold isn't it? You know, I do have a shipment of weapons and armor ordered by the Jarl... perhaps I think I'll give him a little word about that outpost. Surely if they don't need to fight bandits, they don't need the upgrades in gear they were going to get...
I mean, it's not like Skyrim's in the middle of a civil war or anything. Right?
Spoiler
A little context on this build - Merchant builds focus on actually creating things and selling them, rather than for combat. They max out the blacksmithing, alchemy, enchanting, and speachcraft perk trees before they shift their focus to other trees. They prefer to avoid combat as a result, obviously. To add onto that, this character is level five at the time, meaning that even then their skills are rather low, so on master difficulty, getting swarmed by three bandits when your best possible gear is a steel sword you found and some Elven Armor you scavenged off of some thalmor guy who woke up on the wrong end of a bear, and with only potions and prayers to keep you alive... yeah, not exactly the easiest of things. Glad I was doing a potion run as well, or I'd have been boned.

cause I'd sure as heck be using them haha