Why are the Timekeepers so underpaid?
This is just one particular point I felt like raising because, while there are plenty of plotholes and badly written parts in the movie (as in most others, for that matter) the movie specifically went out of its way to tell us how the Timekeepers are scandalously underpaid. Why is that, though? This is a dictatorship which relies on state power to repress a vast number of impoverished, disenfranchised people. It does not make sense anyway. The Timekeepers should be paid well so that they have an incentive to actually do their jobs. They should also be paid well to ensure their loyalty. I mean, come on! If the military is paid similarly, then there should have been a military coup long ago!
It's also extremely impractical. Raymond had to choose between chasing down Will or collecting his daily wages. I'm sure this is not the first time this has happened. Very inefficient! It's not just when you suddenly need to chase someone that this becomes an issue. Imagine a hostage negotiation scenario... or, for that matter, imagine what happens if the Timekeeper's car is stolen/damaged while he is in a remote location, or any number of other situations.
If I were the dictator of this society, I'd make it so that Timekeepers are well-paid and it's one of the most lucrative jobs available (same for the military), while legally or de facto ensuring that they can only come from Zones 1-3 or so (so they don't feel empathy with the poor in the lower districts). Also, rigorous indoctrination and testing, of course. Though it's quite interesting how Raymond, someone who came from a poor background, was one of the most zealous Timekeepers around. Such a shame that we didn't find out much of his background after all, it was a really interesting plot point that should have been developed more. Better yet, just disable the damn time mechanism for the Timekeepers, or if that's not possible, always give them a week every time they go below one week. And for science's sake, make it harder to steal the damn time!