20: Childhood illnesses? Any interesting stories behind them?
When Kakashi was first born he was terribly ill due to him being born very early. Because of this he was kept in the hospital until finally becoming health enough to return back home. Because of this, Kakashi is very focused on taking good care of his health since he has a weaker immune system than most.
Turn ons: Kakashi very much likes straightforwardness, he also is easily weakened to hair pulling, his back being scratched, and being able to assert dominance.
Turn offs: Overly bossy women. Feet. Bad breath. Bad body oder. Women who are taller than him. Those who try to make him be submissive.
22: Given a blank piece of paper, a pencil, and nothing to do, what would happen?
Kakashi would doodle random drawings about Icha Icha.
23: How organized are they? How does this organization/disorganization manifest in their everyday life?
Kakashi is usually organized, even if it is messy, it is an organized mess. It manifests in his everyday life by his use of it for all the reports he has to fill out.
24: Is there one subject of study that they excel at? Or do they even care about intellectual pursuits at all?
Kakashi excelled in all his subjects at the academy and had no trouble with any of it. He cares very much about everyones intellectual pursuits, especially his own.
25: How do they see themselves 5 years from today?
Hopefully with a more secure job as Commander and possibly with a family.
26: Do they have any plans for the future? Any contingency plans if things don’t workout?
He would like to travel in his later future, but if he can't he is content with resting happily in Konoha in retirement.
27: What is their biggest regret?
His biggest regret is allowing himself to get so consumed with the belief that if he didn't follow the Ninja Code in every single way he was trash, it destroyed relationships and led to Kakashi losing people he cared for.
28: Who do they see as their best friend? Their worst enemy?
He sees Might Gai as his best friend. Kakashi has no real worst enemy and despite differences between villains he hardly considers those his enemy as well.
29: Reaction to sudden extrapersonal disaster (eg The house is on fire! What do they do?)
Like anything, Kakashi will be calm and collected towards the situation. It takes something very personal for him to react emotionally towards it and let it really effect him.