The key is Mihawk.
Oda wants us to believe in Beckman vs Zoro.
But, Shanks and Mihawk are both the Pirates Luffy and Zoro are chasing.
Those pairs have always been depicted as close together, so I think they'll end up fighting at the same time. It would be weird for Luffy to fight Shanks, then Zoro fight Mihawk an arc or two later. So, that makes the first few fights easier to plan out:
Shank vs Luffy: CoC/Captain duel
Mihawk vs Zoro: sword duel
Beckmann vs Nami: brain duel
Yasopp vs Usopp: sniper duel
Roo vs Sanji: cook duel