Everyone in this movie is a loser
I don't say that as a knock. It's just an interesting and integral part of the story. The central theme of the movie is winners and losers and as such all the characters go from winners to losers through the course of the story. **SPOILERS BELOW**
Frank loses his boyfriend, his job, his apartment and then tries to take his life.
Grandpa loses his residence at the retirement home, then loses his life.
Dwayne loses flight school.
Richard loses his 9 steps.
Olive loses Little Miss Sunshine.
And Sheryl basically has to be there for all her family members who are going through all this, essentially making their losses hers.
Yet, despite all they lose, in the end they're still okay and maybe even better people for having gone through it all. These characters take a journey, both in a topographic sense and an emotional one. That's what makes this a great story.