I'd really appreciate it if you tell me whether something wrong with this paragraph or not.
~and once, during desperate moments, you realized achieving something you couldn't do for a long time, wouldn't that deserve "one genuine smile"?
I would rewrite it like this:
~and if once, during a desperate moment, you realized that you had achieved something you hadn't been able to do for a long time; wouldn't that deserve "one genuine smile"?