For starters, stop buying spell books for crying out loud, you can pretty much loot them any old place. And yes, the dark brotherhood pays ok. But yeah, the best way to make money fast is 1. Steal from the dead, kill more and take whatever the victim has, right down to their underwear, then sell it all! 2. Hunt and sell your goods. Pick flowers if ye have to, and sell them too. Hold onto the bare minimum. Raid a few Giant camps, Bandit camps, take from them, take from their chests, and do over some tombs and defile the bones that rest there, knock down a few mammoths and rip out their tusks. Go crazy running around Skyrim killing, hunting - and most of all, selling all the plunder! No holes barred! *clears throat* Just don't steal from the living for quick cash. They tend not to like it and selling it is hard unless you are a member of the Thieves Guild. But if you are a member, steal there stuff as well and sell sell sell! Just be careful of the thugs that come look'n for ya on account of being a low down dirty thief.....