Just two questions

1. Of couse he will. His appearence apparently doesent effect him.
I also have a light chaos chao. His stats are all 99. Except stamina.
(The last chao I had with all 99 level stats sorta played a little magic
Trick and I never saw it again. I was sooooooooo pist.) But he still beats all
The computer chao by like three minutes. It rocks at karate too.

2. Somewhere between 15 and 30. You will know by studying it in the garden.
When it's stats are right, you can see it take off and fly. Sometimes out of
The water so be carful not to be jumping around or you may risk knocking
It out of the air.(Unless you are wanting to be a jerk and do it anyway.)
This goes with other things too. Like run, swim, or what it looks like.
Penguins will slide, dragons breathe fire, pigs roll, skunks fart,
Gorillas beat their chest and there is a lot more. But my chaos chao is level
99 fly and still will slowly flutter down on a race, but far enougth to
Quickly go and grab the side of a cliff. (I think it barely starts at level
45. Correct me if I'm wrong.) If you say it's fluttering down because
It has no wings, I have a level 99 shiny fly chao who does flutter still.
They can't just fly up on that cliff on the race.

If you where somehow dissapointed with any of this, sorry. I did my best.

Yeah, it can still fly. I watched this YouTube video about this guy entered his light chao in a race. When the chao got to the Crab Pool, (you know what I mean, the really big swimming pool with the crabs watching) the chao flew over the pool and didn't swim in it at all! The chao flew wicked fast, too. And the other question, I don't know. I got this game not long ago, so my chao isn't that strong.

1.Yes even if your chao doesn't have wing that are big he can still fly,if you build his flying stat up,he will be able to fly.If he has small wings and say his Fly is lvl:35 he can still fly.

2.I think it has to be above lvl:15 on fly for him to be able to fly around.

Hope I helped =)