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What are obstacles you have to writing characters who are a different gender/race/sexuality/any other quality as yourself?
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Other people.

It seems like everyone has an opinion about how your progressive character should be written, even if they share no traits with said character. Some people seem to believe that how you write one character frames how you view an entire group of people. If you make a Mexican character who can't cook, you're saying all Mexican people can't cook. If one of your villains are gay, you're saying all gay people are evil. Some days it feels like the only way to make a "good" progressive character is to make them flawless and infallible, but that's god modding and never makes for an interesting story. 

I'm more going by things I've read and seen elsewhere. I've had no real problems writing characters for this site. most people who are into the hobby of writing have been pretty chill.