@Background Pony #07C0  
Soarin seems to be the guy that is into it not to beat others, but for self improvement. If he loses but his own personal time keeps getting better each year, he is happy with the results.

omg if she wasn’t a cripple, she would be the best wonderbolt

One day there has to be an episode about her.

@Dig Dug  
Then we have Soarin. He’s always happy.

honestly i’m more interested in what seems to be the fleetfoot-spitfire rivalry, plus flitter finally beating cloudkicker after multiple years of failure

This is a fanfiction waiting to be written

Don’t forget, she was also in the hospital.
 
already posted gif

@DanielTepesKraus  
I didn’t notice the little halo. I like how she’s still smiling throughout all the progressions. She’s either a good Stepford Smiler or she’s really good at being optimistic and looking at the bright side of things. (Possibly both.)
 
@Background Pony #6D8D  
At the very least she’s happy now where’s she’s at like OP suggested. (Plus if you add those cute little headcanons of her being a good mother to Dinky or other ponies or her being friends with other background ponies, her life becomes extra sweet and happy despite what happened to her eyes.)

i like derpy’s halo in the last panel.

@mjangelvortex  
OMG! I never even realized that!  
Derpy tried one last time to pursue her dream, only for it to finally shatter completely!

I never liked looking at this progression. Not even so much for the Muffins thing, but every time somepony is disappointed and looks so unhappy. That breaks my heart.

She also attempted to get eye surgery as a teen but it ultimately failed.