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The best way to go on a nightly burglary streak is to wear sneaky clothing. That means dark clothes with low visibilty and noise. Where can you buy them? Well, I suppose a tailor is a good place to start. But usually you'll find sneaky gear on the corpses of bandits you kill.
A high sneaking skill helps, of course.
Leather Gloves, Light Tarred Jacket, Tight Black Hose, Quiet Dark Shoes, Black Hood
There's a Light Tarred Jacket at the Rattay Bathouse. There's Silent Shoes in a Chest in the Courtyard Lodge in Talmberg, i use Brown Pants or one of the Patched Pants (looted - but not the "dark patched pants" those are worse), and Hunting Gloves are almost as good as Leather (Talmberg), and a Black Hood from Divish's Scribe chest (Brown or Grey hood work also)
But you don't need the best - just "good enough" - any dark pants, dark shirt, and boots will get you below (EDIT:5 Noise) "good enough", but i've also stealthed through Talmberg in no clothing at all since it was lower than wearing green & red (Noise of 35 or so i think)
General tips:
Keeping ur noise around 5 or less should be the goal, but this is not necessary for simply lockpicking and stealing when no one is around. With a little effort, 5 is pretty easy.
Lockpicking improves Stealth. Pickpocketing improves Stealth, Knocking out or Stealth Killing anyone improves Stealth.
Once ur Stealth gets above 6 ur pretty hard to detect - even with a Noise of 10+.
You might be "heard" Lockpicking, if someone is nearby, but you will only get "caught" if you are seen doing illegal acts (Lockpicking, Robbing, Pickpocketing, etc.).
Moving slowly while crouching is the least noise you can make.
Have Stealth trained up a bit Before trying to Pickpocket - getting caught pickpocketing is a guaranteed crime/bounty. Do the time, pay the bounty, or only train pickpocket outside of a town. Wayfarers are a good option, but Reputation may still take a hit, and you might get a bounty.
Pickpocketing Sleeping People is Way Harder than it seems like it should be.
Just walk behind the target matching their pace, perhaps by using caps lock, and just go for it (without crouching - as crouching makes you more suspicious to casual onlookers). The target will notice you if you bump into them from behind or you get too far away, or if they turn and see you.
I only point this out because to me that's the way the developers intended pickpocketing to be, but if you read online it gives the impression that pickpocketing is always done on sleeping targets or while sneaking.
It would probably take an entire in-game 24 hour period just to establish that pattern but then you'd have to attempt the job either the next day or night. But you also have to be aware of any co-lodgers who live in the same house who may have a different routine and who may, ultimately, catch you in the act.
When intending to steal from a person in such a pre-meditated way, you'd better be sure they have something of significant value in their possession otherwise all of the time and effort spent would have been for nothing.
I've never used a sleeping potion in the way you are alluding to, certainly never heard of anybody going down that route and investing such a large amount of time and effort for such a potentially small gain.
Thank you for this information and perspective
For a side note, as your Stealth Skill Improves, your Noise is reduced - thus why the statements your gear doesn't matter so much.
In game, with high Stealth skill, 8+, you can wear pretty much anything and have a low noise, as long as you don't wear Chainmail anything.