When should an owner prepare for an expansion cycle?

Before it is obvious. The assets that capture a cycle — a documented operating system, trained people, clean books, proven unit economics, banking relationships — take quarters to build, and everyone shops for them at once when the cycle is visible. Owners who systemise in ordinary months get to say yes quickly in extraordinary ones; readiness is the scarce commodity, not ambition.

From Dubai Is Set for a Big Cycle. Most Owners Will Watch It Happen to Someone Else. — the full reading, with the method behind this answer.