At the point where all the other "normal" mechanisms monitoring storing the job on the queue have failed I would suppose I have a far more greater problem on that system. Personally I would not use flags for jobs types, I would monitor them with flower. Also, we need to keep in mind that it's one thing retrying sending a job to the queue and a whole other thing retrying a job already on the queue that failed for some reason. In my experience so far there a mechanisms that deal with both of these issues effectively and none involved using the webapps database for this.
Thanks, I will take a look at the Pythonic way of doing these things. Celery does look a lot more industrial-grade than most of the Ruby solutions so my curiosity is piqued.