Tbh, I kinda see death flags both for Kuma and old VP, but then I think about the major character's death happening on-screen and not during the flashback I can only remember WB and Ace off the top of my head.
Kuma's case is similar to WB imo, in a sense that WB was beyond saving and chose to die in action rather than in his bed.
I frankly don't understand HOW Kuma can be saved as he is now - wounded, barely hanging to the remnants of his will, probably on his way to save Bonney again?
I do not believe in reincarnation/memory transfer to S-Bear/getting healed. It's extremely tragic imo, so probably Oda won't go all the way and kill Kuma, but I don't know how he is going to manage it.
With VP death flags are still there, but also 2 VPs are already dead and maybe this is it?
And where the hell is Caribou and BBP??