Hi kraed,
I assume you're using a vector art program to make the PNG images that you then import and use in Spriter, but then you want the final product to look like pixel art? (I assume when you say retro and square you mean pixel art). Do I also understand correctly that you are using Spiriter in pixel art mode to create your animations?
It sounds like what you're after is to use the opposite of pixel art (high res art made from a vector program, along with on the fly rotation etc) but to end up with authentic looking pixel art in the game. The only way this would work perfectly is if C2 support an on the fly filtering system that cleanly rotates pixel art while recalculating it to still look like clean pixel art. C2 does not yet support such a thing as far as I know, but maybe there's a shader you could use to achieve this effect.
As for Character Maps, yes it should definitely be possible to have random character generation in C2. First create an assortment of character maps in Spriter for your character that each change just one aspect of the character (hair, shirt, pants etc etc) then use the action "append Character Map" in the Spriter object, and have the game randomly select 1 of each type of character map..one for hair type, one for shirt type etc etc.
I see now while writing this you resolved your "jagged sprites" problem, but I'm still not sure what the problem actually was or what you mean by "cropping". Can you explain that in more detail?
Thanks,
Mike at BrashMonkey