Kuma meticulously planned appropriate locations for each Straw Hat member to assist them in becoming stronger.

Chapter 1099 of the One Piece manga continues the gripping flashback narrative of Bartholomew Kuma's past and reveals many intriguing details. In the latest chapter, author Eiichiro Oda allows readers to explore how Bartholomew Kuma sent each Straw Hat member to specific locations from Sabaody using his Devil Fruit power. Thanks to that 2-year timeskip, each member made a remarkable comeback, in surprising and unexpected ways.
After a long wait, One Piece has finally illuminated one of the biggest mysteries surrounding the timeskip, a theme that has garnered considerable attention from fans since the Sabaody saga.
This chapter discloses that Kuma traversed the world, visiting every island to seek a cure for Bonney's ailment. Among the locations Kuma visited were the kingdom of Turin, Kuraigana Island, Karakuri Island, the Boin archipelago, Tequila Wolf, and even the sky island of Weatheria. These are all places where Kuma sent the Straw Hat members during the timeskip.
This revelation, though seemingly minor, demonstrates that Kuma's fate choices for each Straw Hat member were not random; he carefully evaluated specific information about each crew member.

Kuma's decisions regarding the fate of each Straw Hat member seem meticulously chosen. Despite Kuma's intentional choices, opportunities and fate also appear to play a significant role in the locations where each member resides during the timeskip.
Additionally, Chapter 1099 leaves some unanswered questions, such as Luffy, Brook, and Sanji's destinations being Amazon Lily, Namakura Island, and the Kamabakka Kingdom. This raises the hypothesis that Kuma may have visited these places briefly, hence his knowledge of each island's location to precisely take Luffy, Brook, and Sanji where they needed to be.

On the other hand, while Kuma's decision to save the Straw Hats seems meticulously calculated, fate also plays a significant role. An example of this is Zoro being sent to Kuraigana Island. It's uncertain whether Kuma knew Mihawk would be there or not. Another interesting case is Luffy being sent to Amazon Lily, initially seeming random but turning out to be crucial, with Rayleigh finding Luffy there.
Kuma's story brings surprises and retrospection on the events of Sabaody and the timeskip, a surprising yet beneficial addition for fans. Furthermore, recent developments highlight Oda's ability to create a complex and interconnected storyline, emphasizing the depth and storytelling beauty of One Piece.
Currently, the flashback about Kuma is still ongoing, with many islands and details expected to be further revealed.
