Ah yeah playing the academy phase of the game does get somewhat repetitive. For me I was able to keep things somewhat fresh as I got myself the DLC after I finished my first playthrough. I got to do all the DLC stuff including trying out the Ashen Wolves and their prologues.

I romanced Dimitri on my first BL playthrough and it was great haha. Yeah it would've been nice if he and Claude were also bi. And oh no saving over your Crimson Flower playthrough. I actually have one friend who romanced Hubert on her first playthrough haha (I romanced Dorothea on my CF playthrough).