(Yooo! The opening "Ludum Dare 32 - Track 5" is in my game ROSA! Song buddies! :D)
Super SUPER well-made. The idea behind this is really intriguing. At first I thought the deteriorating environment was literal, but it started to make sense when the main character returned home. I liked the teddy bear as a symbol of innocence and hope. I also loved all the little details sprinkled throughout that convey both story and atmosphere. (Though I have to ask - why is SquishypuffDave in this game? XD EDIT: Oh my gosh, I can't believe I noticed SquishypuffDave but not myself XDDD It's an honour! Thanks!)
As for the reveal, I'm not sure it recontextualizes everything that came before because there's not much story prior to watching the tapes. Or at least, there doesn't seem to be. Why does the main character go to the house? Does he know he's going to do what he does in the tape, or is at least considering it? Or is the tape an unexpected wake-up call on where his life is going? Both those things are probably difficult to convey in such a short game, espcially when you need to focus on the main events. In any case, it definitely works as a reveal for both the main character and the player, whether it be literal or metaphorical.
The only real issue I saw is that there doesn't seem to be a way to exit the Windows version at the end. (Also if I knew my thumbnail would be front and centre, I might have spent more time on it XD Thanks for promoting us all though!)
Excellent job!