Pretty good, OP, a few off moments, but OK on the whole.
>8: areound - should be "around" - thought you were the proofreader!
>8: inadequate - not the sort of word a 14yo kid would use
>9: that home - sounds a bit off, especially with "that school" coming right after. Maybe drop the "that" and just have "home"
>9: an university - should be "a university"
>14: great scholars - you wouldn't use that phrase when talking to a young kid, need to dumb it down, "some very clever people" or something
>14: and for what purpose - again, needs dumbing down for the kid, just say "and why"
>21: a Tokyobound - drop the "a", shouldn't be there, but even "Tokyobound" sounds weird. I can't really get the sense of what he's trying to say in that sentence, so I can't help you
>21: Could it be that you are aiming for - shit, is he supposed to be 60 or something? Just say "are you aiming for", or even "you aiming for"
>21: Let's try our hardest - OK, I know what the Japanese is there, but you wouldn't really say than in English, maybe "Let's go for it", or something
>22: On my own feet - the customary English phrase would be "on my own two feet"
>23: bumpy and curve - "rough and winding" is a much more usual way of putting
These next ones are a bit more subjective. Asuka's words are sounding stilted and over-formal. Of course, that could be intentional if you're trying to give the flavour of a non-native speaker, but if not:
>16: that I was getting off - nobody would use "that" if they were in a hurry, they'd just say "I was getting off"
>18: for how long - "for" should come at the end of the question if you use it at all
>19: could it be that you are - just use "are you"
>20: I will show - use "I'll show"