Easy Money

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If anything, I'm finding that a thief type character, specifically played as a thief, is the easiest path to instant wealth in the game. No need to go traipsing around dungeons looking for loot to sell. You essentially get unlimited wealth from joining the thieves guild, and just doing small jobs for Vex and Mallory.

I think I've tried all of their different types of small jobs now, and seeing as how there seems to be little correlation between which job you take and the size of your reward (they all seem to offer somewhere between 100 gp and 500 gp with 250 gp being the most common), as soon as you figure out which ones are the easiest for you to perform, you just take those jobs. The reward is actually a supplemental part of the money you make, as you invariably steal/pickpocket other items each time you perform a mission. The only rules are don't get caught and don't kill anyone.

Delvin Mallory's Jobs:

The Numbers Job - Change the ledger book at a business. This one is easy, as typically the ledger book isn't in the same room as the shop owner. So if you are quick, you can enter the room with the book, go stealth, and quickly change the book without the store owner looking. Sometimes there's a safebox next to the ledger book to boot, and since time freezes while you pick a lock, you can usually pilfer that too. I find this one has the highest time investment to return ratio.

The Fishing Job - Pickpocket an item from someone. Now that my pickpocket skill is high, this one is also pretty easy. I do this one sometimes, as even though you are only required to take the one specific item, the target usually has a few other valuable items that can be nicked. And you level your pickpocketing skill, unlike in the Numbers Job.

The Bedlam Job - You go to some city, and have to steal enough stuff to reach some gold threshold - like 500 gp worth of stuff, and it doesn't matter what you steal, so long as you reach the target value. This one is a royal pain in the ass. For some reason, pickpocketing and taking items from chests doesn't seem to count towards your total. Which is dumb. If I find a coin purse laying out on a shelf somewhere, it counts, but if I open a chest with coins inside, that doesn't count. Granted you get to keep and fence the stuff you steal, but it isn't like you don't get other stuff from the other missions too. I have done this once, and I don't foresee me doing it again.

Vex's Jobs - these are generally easier IMO.

The Burglary Job - Steal one specific item from a house. Ridiculously easy. Typically when you arrive at the house, either no one is home, or if they are home, they are sleeping. So unless you do something stupid like pick the lock right in front of a guard, it's no problem.

The Heist Job - Steal one specific item from a shop or merchant. This one is also pretty simple, although you usually have to do it at night. Oftentimes, the target item is in the same room as the shop owner, making it very difficult to do when the shop is open. That said, shops typically have a lot of other good stuff to steal, so if you don't mind waiting until nightfall and dodging the guards, it's usually quite lucrative to break in and clean the store out.

The Shill Job - Plant a stolen item in someone's house. Is basically identical to the burglary mission, except that you're placing something there instead of taking stuff from there. (Although you do take stuff you find of course.) Again, the owner of the house is usually either not there or sleeping, so easy to do.

The Sweep Job - Steal three items from a house. Again, since it's not a business the same thing applies here as with the Shill and Burglary jobs. For whatever reason, I think I've only done this one once.

So basically all of Vex's missions are easy, and all of Mallory's except the Bedlam jobs are easy too. The other good thing is after you complete five small jobs in a given city, you get a special quest that unlocks a new fence in the thieves guild, which is good, as hardly anything that I have to sell can be sold to a regular merchant.