So this is a very easy way to level speech and make gold in skyrim and works with any vendor in the world. • First head to any vendor. • Go to their inventory by clicking on their name. • scroll down to your own name and RIGHT-CLICK your name and then drag into the inventory window. • If it worked you should still see the vendor's inventory and be able to sell their own items back to them forever, a very quick way to level speech.
Let me know if you find a vendor with tons of cash!