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Exit-Sequence Planner
Don't start with the thing you most want rid of. Start with the thing you can most safely be rid of. For each line: what depends on it, can you get your data out, the notice period, the renewal date, and a safety score from one (boring, on the edge) to ten (takes your customers' money).
The rule is simple: overlap, never gap. Build before you cancel, run both side by side, revenue-critical last.
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Build it, prove it, then cancel
Run the replacement alongside the old thing for a real stretch, on a busy day, with the messy edge cases your business actually throws up. The overlap money is the cheapest insurance you'll ever buy. And decide your fall-back before you cut: a documented manual workaround, a fast rebuild path, or retained redundancy for the jobs that can't stop.