Adventures in Skyrim - spoilers ahead! In this entry I am following my custom scenario "A Curse of Iron". You can follow the rest of the story here!
I had initially planned to enter via the secret Companions entrance but wasn't able to scale the damn wall up to the opening. The guard standing behind me must have thought it amusing since he just waited there till I gave up before arresting me. Figured that like Riften, this was probably the easiest way in so I surrendered and found myself in Dragonsreach dungeon. Slipped out via the floor grate pretty easily and found the prisoner storage chest within reach from the tunnels below... only my pick broke. Damnit! Slightly frustrated, I left all my gear and cooked food and made my way out of there collecting what I could while sneaking around the guards barracks.
Once top side I was careful to hide behind the houses and time the guard patrol to enter Breezehome and raid it of any useful stuff. This turned out to only be food and hides. Better than nothing, so I used the nearby smithy to make a new set of superior leather armor then snuck inside to steal an iron sword and dagger. Wasn't quite sure how I was going to get clues from the tavern since the guards kept a close eye on the place, so instead I asked Mila, a little girl for some assistance since Tolfdir mentioned kids could detect that same "vibe" I did. She mentioned something about a creepy old woman so I checked the feeble lady first who was very rude but otherwise ok. The blacksmith couple were also fine as were a passing red guard guy and another random lady on the street. Timing these "chats" was getting to be tedious.
Finally an nice old lady named Lilith came by and I knew precisely what the kid meant - she seemed in a hurry to get out of town. I politely bid her a good day and as soon as she walked past I slit her throat right there on the road before she exited the town proper. Then came my grand escape plan. I snuck my way as far as I could to Jovasskr to use the secret wolf exit but was sighted at the upper crossroads near the loud priest, so I ran dodging arrows to the cave door only to find it wouldn't open! So much for that. I tried scaling the walls a few times but that wasn't getting me anywhere so in the end it came down to me sprinting out the front door, being chased by a large group of guards across the field. Must have been quite a sight for the dragon that was circling overhead. Fortunately for me it decided to come down on my pursuers leaving me scott free to escape into the North.