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What do you expect people to do, roll dice to randomly select everything?
It's a game. You're always are supposed to come up with some kind of plan or strategy for the future if you want to do well at a game. That's true for every game from the playground to professional leagues. Even games that seem to be entirely random have large amounts of strategy to them.
Even more specifically Role-playing games in general are games where the reward for playing it (beyond obvious social rewards) is that your character gets more powerful in some manner. The plan for the character starts at first level just by picking a class in Pathfinder.
So there are going to be very few players in this game who aren't going to know what to do after they take their first level of wizard or fighter. They've already made up their minds by making that first choice about a lot of things that need to be thought about for the future.
If you want people to keep gear it needs to be useful to them, not just cool or interesting.