"all they care about is following the letter of their policies."

Thing is those 'desk jockies' (I've known a few myself) are only paid to help you fill out the necessary forms correctly so they can process your application for assistance as efficiently and as quickly as possible. They are not usually in a position to make decisions or judgement calls on individual cases. Those judgement calls on individual cases are far more involved, which is the very reason appeals can take far longer to process. But despite the seeming hassle, appeals are still very much worth pursuing. Don't abandon any appeal that might deliver you some cash, even six months down the line. Even if short term issues are pressing, the long term ones also need to be addressed. Meanwhile, as said, I've actually known a few people who got work at their local DSS office doing that very same desk jocky job of processing new claimants. Have you ever asked your local office about vacancies there? It might be worth your while. In the UK at least the DSS is a very equal opportunities employer which will not be prejudiced against a job applicant because of disabilities or present unemployment status. Plus as you say, so long as you can tick boxes and stay polite when people on the other side of the desk are getting pissed off with you, you don't really need any prior expertise.