Not sure if you get anything by doing 5 quests but are jobs glitched? I got a Bedlam Job that sent me to Raven Rock and I probably stole a couple thousand and it didn't give me credit. I had to go back and quit the job.
I am having the same problem. I thought it might be because I had just finished a shill job for Vex which meant 5 radiants for Whiterun. That meant I got the reputation quest for Whiterun and I am hoping that interefered with the Bedlam job. I am going back to Raven Rock to try once more. If not, I will just back out of the job.