A quick sequel,
Two words: Nerf onesie
At this point there’s no other option except to take Timmy’s legs for his own safety.
With how obsessive fluffies can get the little goober would still find a way to try. I’d vote for taking him to the top of the nearest dry quarry and let him give one more try.
Keep trying Timmy! don’t let those dreams be dreams!
Timmy is an unusually durable fluffy.
There’s no denying the sheer dedication of this man
i think timmy would do good with a vr set and a fan pointed towards his face lol
Hmm perhaps one more happy sequel…
Could probably rent/buy a fan big enough to keep them suspended.
Im sure nothing could go wrong. 
Sadbox sequel: Sniff
“You did it timmy, you’re finally flying.” Owner releasing a handful of ashes onto the breeze.
Ghost of timmy traveling on the updraft with a smile.
Oh, I like sadbox sequel.
My take, which could be any box, is that Timmy gets to fly–once. He gets to choose when.
Then launch him into orbit. (Cue Major Tom)
Just tell him he flew, and that he hated it
Or better yet just take his wings then he might actually get the idea that he can’t fly anymore… Although you can never underestimate how stupid those things are.
You can do it Timmy don’t be sad
Take his wings or rig a harnass where he is lifted half a meter off the ground so he has the illusion he is flying.
It’s not the fall that kills you, it’s the sudden stop at the end.
“Nu kitty munstah, am fwuffeh…”
The universe suddenly realizes it’s mistake and retroactively takes back all excess lives, causing Timmy to die on the first attempt
Well let hem try again if he die, then he die.