I've come up with how I'm going to go about payments - Tokens. I'll have it so that jobs don't pay out a single token, some pay multiples. A token is worth 20 septims in the Very Hard version, 40 in hard, 80 in normal, 100 in easy, and 120 in very easy. Tokens will be redeemed at a machine inside each castle. (or, in the IC's case, a booth in the market district) I don't know how to set up an NPC, but I do know how to set up a vending machine.
Anyways, I can start setting up the jobs around Cyrodiil now. I like the idea of a token system, because it reminds me of tokens that shopkeepers would give out to sharecroppers instead of cash, forcing them to come back to that shopkeeper for business. Except, mine will have a gold value attached. The tokens can be sold to regular merchants, as well, so if you're in a pinch and can't get to one of the machines, you can use them instead.
:EDIT: After looking into it, I don't think I'll be able to increment the player's skills in tiny amounts without using OBSE. I don't think I want to go that route yet, though I'm sure someone might decide to take up the torch on something like this and do it.