No really big heist or killing spree. I do take pride however to sneak in and out of places without detection. No, wait. That was before I got 107% chameleon

I just did Sanguine's guest the first time. There i was, in Leyawiin, no money and only jail clothes. Being a Prowler in the Thieves Guild, no reason to worry. I looted containes around Leyawiin to afford to buy a lockpick from Dar Jee, after that proceeded to rob the Fighter's Guild. I stole some nice clothing and available weapons from the basemant, then proceeded to pickpocket a leather armor off a khajiit sleeping upstairs. Before the sun rose, i was riding towards Bravil fully equipped.

Totally worth it for seeing
I wonder why she didn't introdcue my khajiit to the torture chamber for that? :hehe:

Feshly joined the Thieve's Guild, going to Bruma, and then in exactly one night, clearing out the entire town of everything. I even took their baskets.

Once you have that 100% Chameleon, you can do almost anything, so I'm gonna hijack this thread as my best heist:

Let me change it to "what is your idea of the best possible heist?" I'd thought of pickpocketing all a city's guards' armor from them as they sleep and replacing it with permanent bound armor (zero-weight so you can RPP it) and having the entire town patrolled by "Daedra". I haven't just because it would take too long to accumulate enough equipment for them.

I know you were making a joke, but what's sad is that a cheese wheel is about as valuable as loot gets.

I'd like to do that with at least one town. Having the town patrolled by Dremora would be cool.