Cursed Hills

 my thoughts while reading your comic, presented in semi-linear order:

*start reading comic*
Oooo! this looks like the raw emotional confrontations upon which some official silent hill stories are based
woah her facade is cracking, I wonder what kind of repressed terror lurks underneath
... THERE WASN'T A MONSTER INSIDE!?
that is LAME-SAUCE of the HIGHEST CALIBER /
*finished reading*

I'm not an expert on Silent Hill so dismiss my opinions if you want. Also I'm being way too harsh. sorry.

Anyways, I think you missed two opportunities here. Keep in mind that the identity we assign to others doesn't always match their own self image...
IF LENNY'S INSTINCT WAS RIGHT: 
 Revealing your true self, with all your issues and transgressions, to someone else isn't easy. But if you try keeping it concealed then that causes people to make mistakes about you and that makes things so much worse. Instead of crumbling to fragments, Cali should become what she feels herself to be (a killer? disgusting? dead?) and that should scare Lenny. Later on Lenny could come to regret his reaction and try to seek out or save Cali.
IF LENNY WAS dead WRONG:
 In silent hill, reality is subjective and is particularly spiteful. That place is alive, it feeds upon real sins and human errors and gives birth to dangerous effigies. It forces visitors to relive their darkest moments, when they are at their most weakest, and that's when it attacks.  You wouldn't have to change this comic but you should make an addendum where Lenny gets dragged away into the dark and violently reborn amongst filth.