Wow. This game gets pretty deep and depressing. Pretty well made and lots of interesting ideas here. The voice acting is pretty good as well.
It's seems to me that there are a lot more bad endings and some of the "good" endings are not entirely good. Makes me feel that part of the point of the game is that these situations are not easy to deal with.
I made a video of my playthrough, didn't get quite all of the endings but at least I saved him a couple times: