Here are some techniques that will allow you to quickly and easily achieve high level Sneak, Pickpocket and Speech skills. Very handy if you’re a stealth/thief type character and enjoy playing the game like that. All these can be done early in the game so it doesn’t matter how high or low your character level is.
Easy level 100 Sneak skill
Leveling a skill to 100 would ordinarily take dozens of hours of natural gameplay, but if you want you can actually do it very quickly at the beginning of the game. As soon as you enter the city of Whiterun, find the second guard barracks. It’s not the one across from the blacksmith; it’s the other one. If you’re having trouble finding it even after filling in the city map by walking around everywhere, then you can get there by saving the game and getting arrested, then breaking out of prison and the building you exit from is the one you want. Make a mental note of the location, reload the game to before you got arrested and go there.
Upon entering the barracks, use the ‘wait’ feature until the time is gone 10pm, then make you way to the guard’s sleeping area at the back, activate your crouch/sneak mode, and simply sneak back and forth without doing anything. There will probably be two guards who don’t go to sleep and will detect you when your Sneak skill is low, but they don’t attack so it doesn’t matter. Just by moving back and forth like this you will begin to rapidly increase the level of your Sneak skill. Soon you’ll be so good at it you’ll be able to sneak right behind the guards and they won’t even know you’re there. Eventually your Sneak skill will be high enough that you will be able to leave and play the game normally as a very good stealth character. Or you can stay until you’re at Sneak level 100.
Rapidly increase Speech and Pickpocket skills
One of the lower perks in the Speech skill tree is the ability to bribe guards, which saves you from jail time for any crimes you happen to commit. Once you have this perk, there is a way that you can also use it to level up very quickly. Immediately go around pickpocketing people. It doesn’t matter what you take, as long as the steal is successful you’ll gain points in your Pickpocket skill. When you get caught, make sure your weapons are sheathed and just wait for a guard to arrive. Given the option, bribe them to look the other way. Unlike persuade and intimidate, this speech option will never fail, and will give you a big boost to your Speech skill points.
You can’t do this in the same location over and over again, however, so you have to go around various cities, towns and villages leveling up your Pickpocket and Speech skils, then eventually circling back around and doing it all over again.
A higher Speech skill will allow you to get much better prices when buying and selling from merchants and sell any type of item to any type of shop. A higher Pickpocket skill will allow you to steal some very valuable items – if you’re that kind of character – and deprive potential enemies of their weapons before they turn hostile.