A contractor sees the part they sell. Your plan starts with everything in one pass, so the roof, the grading, and the mechanical room are judged against each other instead of one at a time.
Roof and flashing
Seal detail at the valley. Watch through spring.
Monitor
Grade and drainage
Soil sits above the sill on the north face.
Now
Windows
Glazing putty failing on the west elevation.
This year
Walk and steps
Settled slab. Group with the drainage work.
Later
Illustrative annotation. Not a specific client property.