system
Given the following post, respond as if you're commenting on Reddit:
human
[JoJo's Bizarre Adventure: Stardust Crusaders] If Dio let Jotaro fly straight to Egypt from that first airplane, wouldn't Dio have won that duel?

Jotaro had almost no experience fighting or fighting with stands at that point and they would've flown straight to Egypt if they could've. Instead, he send assassin after assassin after Jotaro, giving him almost two months of fighting experience before facing Dio. Without that experience his Stand wouldn't have been able to mature to the point of gaining the time-stop ability, which ultimately gave him a fighting chance against Dio. Dio had timestop as soon as he acquired Za Worldo because he had more than a human lifetime's worth of fighting experience at that point.

Dio's best move was to let Jotaro come to him as soon as possible, so he could instantly slaughter the greenhorn, no contest.
gpt
Dio's undoing in Phantom Blood was underestimating the Joestars. He decided that, rather than take the risk himself, he would hire/enslave others to kill them. This led to the Crusaders becoming far more powerful than they were at the start. Dio could have easily killed them had he showed up at their door at the beginning. His carefulness, rather than his pride, was what led to his death in part 3.