So I decided to restart the game as J'derras. Using the Live Another Life mod, I selected "I was attacked and left for dead."
I start north of Half-Moon Mill, north of Falkreath, next to a dead Khajiit with a Skill Book, no weapons or anything else other than clothing. I gather some ingredients being an alchemist, and I see four Thalmor soldiers heading north on the road (I'm hiding, since this is a roleplay, and J'derras is being hunted by the Thalmor). They don't see me, so I cast a Fury spell on a couple of them and watch the chaos insue. After a couple of them are killed, they move on. I sneak up and take the armor and weapons of the dead. I cast Fury again so there's only one left, which I then kill face-to-face.
Sastisfied that my enemies are dead, I head towards Whiterun, where I see a dead noble and bodyguard underneath their horses, where I find an enchanted necklace and other valuables. I continue towards Whiterun, passing by Imperial Deserters and Hunters (I also have a mod that increases roadside encounters), then I'm attacked by a thief. I was actually taking a bit of damage, and I didn't have the Healing spell or potions of healing. Then, the Hunters and Deserters start pelting the Thief with arrows and he starts running for the hills. I chase him down and kill him, where I get more nice stuff.
All this before I even get to Whiterun, and I already went from rags to riches by mere chance and wit. God, this game is fun with mods!