Trace the uphill side of the drawing
Imagine rain moving down the slope toward the chimney. On the high side of a wide obstruction, runoff must turn and pass around it. GAF illustrates a cricket as a shaped feature behind the chimney that directs water towards the sides. The roofing and flashing still have to meet correctly where those surfaces join. A cricket is not the cap at the flue opening.
Identify what the roofer intends to keep
An existing cricket can remain while its flashing is renewed. Another proposal may change the cricket shape, open roof covering and alter the surrounding weather layers. Ask the person writing the estimate to mark what stays, what is removed, and what makes the existing shape unacceptable. An indoor stain cannot answer any of these questions on its own.
Resolve the meeting between two trades
If the chimney masonry is also being repaired, identify the edge into which counterflashing will fit, and who will prepare and finish it. Does one quote assume that the second trade has already opened the roof? Who is responsible if the proposed crown repair changes none of the uphill drainage? Ask for the junction detail before picking a start date.
Separate design requirements from a sales statement
GAF's guidance is an example for roofing systems. Whether a particular roof needs a new cricket depends on that roof, the size and location of the obstruction and the requirements that apply to the work. A photograph of another house cannot set that requirement. Have the roofing professional identify the basis for its recommendation in writing.