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Raylong
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For the second task, the Higher/Lower,
do you have to reach round 15 or made 15 correct guesses, spread
out over multiple games?

You have to make 15 correct guesses in
the same game, not spread out over multiple ones. So you
have to reach round 16 (yes, 16, because - just as Atavan already
hinted at - you have to pass round 15).
.gif above ©Haikyuu!! official anime

That would be the Gem Collector if I remember correctly but I could be Wrong.
5 Flying and 5 Dragon gems though will be needed