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How do you plan anything that needs a longer-term view than two weeks (which is most software development except web apps)?

[proc0]

If doing scrum, you don't do the long term estimating. You have goals but they're not slotted into a timeline, instead they are iterated on sprint by sprint until it's done. You can do projections but even those have to be taken lightly because the point of sprints is to change direction if needed.