TOPIC: Grading - do you ever recommend an evaluation by a specialist?

Screw the listing agent. The work is not that big of a deal.

Damage to the building "IS".

If there are no water intrusion problems, this is less of a problem and just something that needs to be monitored.

If there is water intrusion, it must be corrected at its source, not by adding $17,000 worth of interior drainage work!

sounds like a simple french drain, which is fairly inexpensive, could correct this issue, or prevent it from becoming one.

I know I'm late for the party , but Mike this type of issue is common just like planting to close to foundation, flowers like shrubs should be a min of 12 in and trees at least 20 ft not a good idea to be watering the foundation unless a soil engineer wants that, but if you see a area where the soil is separating from the foundation , or depressed areas , these could be clues to a subsoil soil problem
grading however is for the most part a diy project

Mike, you mention the grade was right up to the bottom of the siding. Current requirements call for siding to be at least 6" above grade.
Answer to recommending a specialist- I wouldn't recommend a specialist. I am a specialist as an inspector for grading purposes. I know if the grading, drainage is correct. If it's not I call it out as deficient and that corrections are needed. It's not like needing a licensed electrician for further evaluation.