These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Jerkass Woobie: Sylvia. Probably the least sympathetic of the guards to begin with, but she gets a few TearJerkers. Her first husband commits suicide due to financial pressure and her second tries to murder her for money.
Many of the jerkass characters have Woobie moments at some time in the series; Denny Blood, Shell Dockley, Buki Lester, Maxi Purvis, Snowball Merriman, Di Barker and Al Mackenzie being the most obvious examples.