As a messenger I have carried millions of dollars and many packages containing cash deposits that would exceed your daily receipts by a huge margin.
Was never worried as anyone who might try and roll me would have to be able to ride at 50 kmh to catch me and I was always in a very public place which made me a very hard target.
Walking would put one at far greater risk methinks.
I am sure the thieves know how much $$$ the messengers are carrying but we are mean little SOB's and getting what we have would be a tall task.
If you are making regular deposits pay attention to anyone who might be checking you out to determine a pattern... one might want to alternate between nightly and early morning deposits and even better, do them all in the daytime as the night depository is like a beacon to criminals.