But, as a TSO...did you make anyone go back out and do it again (at your current airport)?
No, but I work at a fairly large airport now, so the standards are pretty lax.
At the most, if I have to open a bag to check the sizes of LGAs within, I'll explain to the pax that if they follow the rules -- put their stuff in a baggie and put it in a bin -- next time, we won't have to go fishing around amongst their underwear and whatnot if we need to take a look! Most seem to appreciate the sensibility of this suggestion.
As far as flying -- when I flew out of my old airport last year, I'd see TSOs I'd worked with in '05 who had hated their job, but they were still there! Always made me sad.