I think it should come down to due dilligence (hope I spelled that right, I'm at work so no spell checker), did the person at least make some sort of effort to be prepared.
We went down into southern ohio this weekend (Hocking hills area) and went down a couple short hiking paths. We saw a lot of people hiking in flip flops and tank tops on a posted difficult trail, one lady in a long dress, another carrying a baby. Then you see the others with backpacks and hiking staffs. If I had to rescue someone I think I'd be more inclined to charge the ones in flip flops than the ones that are more prepared.
We get funny looks sometimes due to my 20lbs of Camelbak backpack bu I'd rather go prepared. People do think my 5 year old is pretty cool with his backpack on. Some might think it not to smart of me to take my young kids on a difficult trail but they have already started to get bored on the easier ones.