You know, i just thought about it why a few of the members are there that i didnt mention in my previous post.
Luffy - Even though the story revolves around him, luffy just needs to get STRONGER to protect his crew in the new world. Kuma was somehow aware of luffy's un-mastered haki, and preferred him to learn it from another whom already mastered the same haki type. Although at one point Blackbeard admired during luffy's gear 2nd battle his impressive haki, it's still not good enough. Infusing a mastered haki + gear 2 or 3 will have more powerful results. 20 points to kuma
Franky - This one is quite easy to figure out, after realizing there's an android now made from stronger material, franky needs to CONSTRUCT better and stronger. Hopefully by paying a visit to vegapunk's old house, he can achieve better knowledge of construction. Who knows, maybe he can rebuild a majority of his body using the same material from Kuma's design. In addition, learn secrets revolving around seastone. C'mon guys, if franky in the past was walking around at one time with the blueprints to reconstruct the pluton, imagine what else he can do with just an opportunity to learn more. Do your best pantyman! 10++ points for Kuma
Sanji - That running from those men are good training for his legs. Sanji already has speed, he just needs better FOOTWORK. Sanji is also a flirt machine, he needs to worry about the number of zeros in his bounty than the number of women he thinks he will get. 10 points to kuma
Usopp - It's extremely obvious, BRAVERY. Knowing usopp, he has very little of it. Eating fruits that are capable to eat him is a start mr lying long nose. One day when he meets Yasop again in the new world, Usopp needs to show him and the rest of the New World that the coward days are over. Remember Luffy vs Usopp? we need more of that type of bravery. 10 points to kuma
Robin - Apparently she is the ANTI-SOCIAL person of the group. In most of the group shots she is sometimes the only person not smiling. Where she is at now, she needs to learn to put her troubled past aside and understand that she needs to fully open up more. Being exposed to the horrors of slavery everyday life should do it. At least Robin has the opportunity to sail seas and visit many islands. 10 points to kuma
Nami - Well this is an easy one, Nami's current ATTACK AND NAVIGATION skills aren't enough. While staying at an island Blackbeard himself at one point thought was a legend, Nami now has the chance to learn attacks and think like a scientist now in navigation using "weather movements" and not a silly compass. Reference: Some sailors in the past times relied on the North Star to help determine where they were.
10 points for kuma
Brook - Im still quite unsure about this one but this is a wild guess. Apparently Brook can sing people to sleep, how about sing them to death? I think it will focus on playing MUSIC for even more deadly purposes. just a wild guess.
10 points for kuma
Zoro - Out of all the crew members minus luffy, i highly feel zoro should learn haki. In the meantime zoro can train by cutting up ghosts. Zoro can pretend these ghosts are different types of logia users that are untouchable. Being able to stop an untouchable enemy is one step forward in better a better SWORDSMAN.
Chopper - I need more info.
In the end, i dont really know how in the world kuma figured out each SW crew member's personal traits, but i dont think it was an accident either. It's like Dragon had an anonymous meeting with Kuma to tell him to perform such a risky task.