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WARNING!!!! SPOILERS!!!
First off I wanna say if youre taking the time to read this... Thank you. Secondly this will be done completely random so the reader will have to peace it together.

My theory behind the ice and monsters: When everything freezes over I believe that it is because Harry has come across something he cannot accept and so he stops thinking(thus the ice and the freezing over) and proceeds to run from his problems(the monsters represent the problems). The flares represent his "moment of clarity" (a "moment of clarity" is when a person thinks clearly and does not feel the effects of stress) which keeps all of his "problems" at bay for awhile before he begins to stress out over his problems. As the game progresses his problems build and build which explains the massing of more monsters with each chase.

Dahlia and the story biggrin ahlia is your girlfriend and wife and ex wife(and Cheryls mom). All the times youre with her youre reliving your past experiences. After you and her split. You end up dating Rachel(the nurse) but that ends badly(hence her "death" wink Michelle is still an enigma to me. Shes either the physical manifestation of you and your ex wifes relationship or shes a girl you befriend or date and she just got out of the same situation you and your ex wife did.

Cybil: I believe in the game Cybil represents your conscious and subconscious. I have nothing to back this claim besides pure intuition.

Cheryl and shadow girl: Shadow girl is Cheryl and her past experiences being relived by you. The pics and vids are all of Cheryls experiences. After you and your wife split she goes through the problems most children go through after divorce. Rebellious behavior, attitude problems, and finally she goes extreme and creates her fantasy hero dad(who has actually been dead for 18 years).

The endings: Each ending correlates with the whole story. The ending the Weak and Wicked is before they divorce and it shows all the problems. The ending Love Lost is when hes moving out after the divorce and its the second part of the story.
Because of the stress of the divorce Harry becomes a drunk which introduces the next part Drunk Dad. Finally Harry decides to move on and because hes fallen on hard times turns towards women for comfort which introduces the last part. Sleaze and Sirens.

If you have any questions message me.