User blog:XAirBorneHellx/How to Make Easy Money and gain Items:

HOW TO MAKE ALOT OF EASY MONEY, AND HOW TO GAIN ALOT OF EASY ITEMS: Skyrim

The first step in the process of this is to find a faction that you like the most and will choose to live in. Second most, choose a city so if any bounty hunters come after you, the guards will help fend them off.

For example, I chose the live in The Rift, in the city Riften. I made sure that my wife (in the game), Sylgja, lived in the house in Riften. Next, I gear up, get alot of my best weapons, and fast traveled to White Run, where I started pick pocketing Guards to get my level up and get rare items. Then when I got caught, I let all hell break loose. I kill all the guards and as many people as I can. And when I've had enough, I leave. Don't Worry about bounty, because you will be living in a different faction. (unless of course you chose to live in WhiteRun in which it is not a good idea to raid there :3) Then you can just go raid where ever you want throughout Skyrim and raid.

I StRoNgLeY recommend you NOT raid everywhere except where you live. Maybe leave two or three factions alone so you have a few places you can choose to move to if you wish.