Liked the multiple endings.
Felt like the ending didn't match the title.
Because it seemed like he went up to heaven when you made him happy and he realized he could only make himself happy.
Then shouldn't the title be: Help Jack go to heaven or something?
By release his soul

No matter what you do at the end the dialogue is the same other than this the game would be good

I suppose this is a demo, because I actually tried to do everything in the game to make him happy but his last answer is always "Only I can make myself happy, thank you, goodbye".
Other than this, you deserve at least these 3 stars for the idea.

EDIT 20/05/2020: why did i not understand the meaning lol (changed it to 4 stars)