This sounds like an excellent idea to me! I believe RIn and I are both planning to play our characters as seniors in the Senior Cycle (Rin, please feel free to correct me if I'm wrong?) and as... not quite strangers, but definitely more on the level of acquaintances that run in different circles. Kira is probably going to be much closer to the kind0hearted nerd from Setsuna's Dream World, albeit with some barely repressed anger issues and a sense that Something's Missing. (I'll let Rin detail what her plans are for Katou.)
Perhaps Rosiel could be Kira's English teacher, or the teacher that runs the Literature Club that Kira's a part of?
Regarding the crossdressing... that is a tough one. Maybe go with what you're comfortable with. AS can be kind of a hard series with stuff like this because of tone... and the fact that it's a work that's very much a product of the 90s. I know that there will be aspects of Kira's canon personality--like the insults to gender divergent or non cishet people--that I will definitely be avoiding/not including in his portrayal (but that's sort of a different thing and only meant as an example) because I am not comfortable with it, nor do I want to risk offending anyone else.
no subject
Perhaps Rosiel could be Kira's English teacher, or the teacher that runs the Literature Club that Kira's a part of?
Regarding the crossdressing... that is a tough one. Maybe go with what you're comfortable with. AS can be kind of a hard series with stuff like this because of tone... and the fact that it's a work that's very much a product of the 90s. I know that there will be aspects of Kira's canon personality--like the insults to gender divergent or non cishet people--that I will definitely be avoiding/not including in his portrayal (but that's sort of a different thing and only meant as an example) because I am not comfortable with it, nor do I want to risk offending anyone else.