Ah, memories. Yes, common perfectionist phase and yes someday it will pass.
I agree with the suggestion that it can be a flag that fewer choices may be better. It is easy to get into that habit with preschoolers and continue it beyond when it makes sense. I'd scale back on that a bit and see if it bothers him.
As far as the train station situation, I would feel fine with saying "you know a lot more about trains than I do and frankly I don't have strong opinions about what choices you make." It is also fine to ask "what's the worst thing that will happen if you choose a train station and regret that choice later? What would you do?"
