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.
The Woobie: Bert Kling. Hoo, boy. To say he has bad luck with women is an understatement. One of his girlfriends, Claire, is shot dead in a book store. His wife Augusta is kidnapped on their wedding day, he later has a Heroic BSOD after catching Augusta in bed with another man, and his colleagues worry about him committing suicide. His relationships with Eileen and Sharyn don't work out either, the former due to Eileen's issues and the latter due to Kling not being able to trust her, which Sharyn thinks is due to her being black.
Eileen herself is one of the most sympathetic characters in the series. After suffering a horrific rape, she has a lot of psychological scars, which worsen after she poses as a prostitute in Tricks in order to catch a man who was killing prostitutes, and she loses it and shoots him dead.