Food: Earth-Luna L5 is the best place to look for food and getting his fenspace feet wet so to speak. Even early on L5 was populated.
Bigger ship: Again L5 or Luna. Depending on when exactly John Henry is opened, he may be able to get/build himself a bigger ship there, if he is willing to pull his weight.
Explore: Nicely ties into the Bigger Ship thing. If he manages to get a Trekkie sensor system, he might be able to go exploring the belt and act as propspector, selling the orbital elements of interesting asteroids to miners to make money and eventually buying a larger ship.
Bigger ship: Again L5 or Luna. Depending on when exactly John Henry is opened, he may be able to get/build himself a bigger ship there, if he is willing to pull his weight.
Explore: Nicely ties into the Bigger Ship thing. If he manages to get a Trekkie sensor system, he might be able to go exploring the belt and act as propspector, selling the orbital elements of interesting asteroids to miners to make money and eventually buying a larger ship.