The resolution cliff nobody warns you about
Tracing runs against imagery sampled at a fixed scale. That works until the roof exceeds the radius the sampling can resolve, and then the failure is sudden rather than gradual: the trace collapses, bleeds into an adjacent structure, or returns an area confidently wrong by a quarter.
The reason this is dangerous rather than merely annoying is which roofs it hits. Small simple roofs trace fine. It is the large, multi-structure, high-value jobs that fall off the cliff — the ones where an estimator most wants the help and is least likely to re-measure by hand.
The fix is to scale sampling with the roof rather than holding it fixed, cap the vertex budget so an outline stays a roof and not a noisy polygon, and clip bleed into neighbouring structures explicitly. None of it is glamorous, and all of it is the difference between a tool reps use and one they stop trusting after the second bad number.
