Completely agree with crossedwires on when it's easier and when it's harder. A while ago dark_agenda did that Racebending Revenge Challenge, and while the story didn't really work so I haven't posted it, I took on How I Met Your Mother. The swapping itself, though, worked very well because it's fairly ridiculous to have a sitcom set in New York and have only white people in it. I think I'd add most sitcoms and mainstream network dramas like Parenthood or Brothers and Sisters or even The Good Wife to the SF/F and comics that you can race or gender swap and have it still work.
(I'm thinking about racebending Castle, suddenly, and the only aspects of it that I think would significantly change would be Martha's career and Castle's upbringing, and how Martha not knowing who Castle's father is goes from some hippy dippy "she's an artist" thing to an unfortunate stereotype. But Beckett, Ryan, Esposito, even Alexis and Castle, wouldn't be that different. Castle is wealthy, yes, but he writes successful pulp mysteries and he's the son of an actress; he's not a blue blood.)
But gender or race swapping something that runs on the idea of gender and race privilege of course is going to be messy because the source is self-aware. If the point of the thing is to note when and how we are unselfaware, well, that really isn't the issue for a show like Mad Men, which is doing a thing and knows what it's doing for the most part. (And changing the race or gender of Betty isn't really going to highlight the ways in which the show treats her badly, I don't think.)
So to that end, I'm not sure if using the swap as a tool to test fail is always going to work. It might help to see fail that you didn't realize was there, but if your writing is actually trying to grapple with various -isms, then maybe what you need to do is swap on the axes that you aren't using. For example, what would happen if you changed the character's sexual orientations, and not in the no-consequences slashy way?
no subject
(I'm thinking about racebending Castle, suddenly, and the only aspects of it that I think would significantly change would be Martha's career and Castle's upbringing, and how Martha not knowing who Castle's father is goes from some hippy dippy "she's an artist" thing to an unfortunate stereotype. But Beckett, Ryan, Esposito, even Alexis and Castle, wouldn't be that different. Castle is wealthy, yes, but he writes successful pulp mysteries and he's the son of an actress; he's not a blue blood.)
But gender or race swapping something that runs on the idea of gender and race privilege of course is going to be messy because the source is self-aware. If the point of the thing is to note when and how we are unselfaware, well, that really isn't the issue for a show like Mad Men, which is doing a thing and knows what it's doing for the most part. (And changing the race or gender of Betty isn't really going to highlight the ways in which the show treats her badly, I don't think.)
So to that end, I'm not sure if using the swap as a tool to test fail is always going to work. It might help to see fail that you didn't realize was there, but if your writing is actually trying to grapple with various -isms, then maybe what you need to do is swap on the axes that you aren't using. For example, what would happen if you changed the character's sexual orientations, and not in the no-consequences slashy way?