Spoiler Any suggestions for the master thief?

[ConfusedPenguin]

Hello there everybody.

Hi.

Right so, just finished the Thieves Guild quest line, became Nightingale, met Nocturnal, made a bit of gold, brought the Guild back to its former glory and whatnot. This is not my first character to do so, but this is the first one to actually still be played afterwards. ( His name is Isilqor by the way, nice bloke, for a Master Criminal.) So I - well, he - intends to become an excellent rogue, furthering his skills with the bow and creating poisons to use at his disposal. But the bit is I still want to be a a thief , but I feel simple thievery is not good enough any more. Something with a challenge and is worth a lot would be more suitable...
So , any suggestions for self set thieving quests to go on , or just something to steal?
Cheers.

 

[DarkEastwood]

I like robbing places, that aren't meant to be robbed (ex. Bandit Hideouts). Ofxoirse, this only makes sense if your character doesn't kill people (which is the most fun and challenging type of thief imo)

 

[ConfusedPenguin]

Yeah, I prefer sneaking about as a thief rather than killing everyone and taking their stuff. But it needs to be a lot bigger and more challenging than a simple cave or castle with uninteresting items in them that I've stole many times before.

 

[Neveraine]

You could try to sneak attack lots of people in towns and then loot their dead corpses.

 

[ConfusedPenguin]

That's what separates the Thieves Guild from the Dark Brotherhood but.