Ask both estimates to describe the existing condition
Request a clear account of the area involved, the material being retained and any earlier repairs. If photographs are supplied, ask which features support the recommendation. A close-up of one crack may leave the rest of the crown outside the picture; an explanation of the whole proposed scope is more useful than the image alone.
Distinguish a repair from a new crown
Ask whether the proposal preserves the existing crown, removes only part of it or replaces it more broadly. The work description should explain preparation and the intended finished result. It should also identify whether related flue or masonry concerns need a separate recommendation. Avoid comparing a product name with a complete scope of work.
Check what the recommendation does not address
If the request began with an indoor leak, ask how the crown finding relates to that symptom. Flashing and other exterior components may need separate consideration. A crown decision should not quietly become a guarantee about every possible water-entry route.
Make an approval note you can use later
Write down the selected scope, the reason for selecting it and any remaining issue to revisit. Save that note with the estimate. If you are not ready to approve, ask which additional information would resolve the uncertainty rather than requesting another coating solely because it sounds less disruptive.