Pretty good, you're really developing the whole dynamic here. Good thinking on the optional S-link with the Twilight date.
What we've done for Twilight is that she has 10 S-Links that work s non-bimbo. Then after that it's her bimbo arc, if the player chooses to bimbofy her. So yes yes the normal path and the bimbo path are seperated. Cheerilee can maximum reach bimbo level 5 in the normal one.
Of course you don't have to do 10 S-links for cheerilee if you wish to proceed to her bimbo stage already. It's just a demo afterall.