Well, I don't know how I've missed this thread.

Lots of thoughts on it but I think if singing songs which express an attitude which offends you, its usually not too difficult to find ones that do. I used to sing Annachie Gordon (occasionally as its so long) because I believe that even though the end was so tragic, it was Jeannie's way of refusing to conform. There was no way she was going to sleep with this bloke, even if she had to die. So she died, which I think took some strength.

I ma now much more likely to sing Jock of Hazledean (ironically written by a man - Walter C. Scott) because she gets to run off with her lover.

The whole issue is so complex.
You get songs that are offensive to many people
You can get songs which reflect society as it was at the time.
You can get songs which reflect how society might have been but in which the characters use their own consciences to act (The horn blower in Matty Groves for example).

I find the whole topic extremely exciting and only sing those songs which make the hairs stand up on the back of my neck - and even then there's too many to choose from.