I felt bad for Khajiit in Morrowind, what with the whole slavery thing. In Oblivion and Skyrim, I have much less sympathy for them, since 99% of them actually are the smuggling, thieving, drug-dealers that everyone thinks they are. I mean, you get invested in their plight, talk about how unfair it is that they are all stereotyped as thieves and smugglers, then you find moon sugar or skooma in their things or find out they're associated with the Thieves Guild or get assaulted on the side of the road in Cyrodiil. Sure, there's a couple good ones, but they are statistically insignificant.
No, it doesn't make the stereotype of an entire race fair or right. But it does ensure that I feel little to no sympathy for the situation.