Help for siding repair

Attached pix from a piece found on a home with siding approx 20 years old. What is it?
Several areas around home soft, spongy with many nail pops.
The handy-man hired to only patch the nail pops for the seller finds that trying to spread the latex caulk over the pops and some exposed subsurfaces just scrubs the thin outer finish off exposing a very soft fiberboard-like material underneath.
He is wondering if he should continue caulking or…?
Handy-man has also been supplied with a few spare boards to replace rotted sections. Seller also plans to have cement board attached to lower 5 feet of exterior in some areas and attaching (thin brick).
Any suggestions to give the Handy-man.
Also I did not do the inspection and just looking around the garage (electrical, fire-code) and the exterior I wonder who did the inspection and what was noted on his report??!

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Looks like a textured Masonite product. Does not hold up well to moisture once paint fails or if it remains in a damp location where it does dry out quickly.

Wasn’t there a class action suit against Masonite? Was that siding or roofing?

Yes. Sorry “Masonite” was used like “Kleenex” in this case. Here is web site with more info and help in identifying siding.

http://www.hadd.com/masonite/faq.shtml

It looks like the siding in question is Boise Cascade from the symbol. Here is the photo and description from the site.

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Boise Cascade
This is from a home built by Village Builders in the mid 80’s with Boise Cascade 12" lap siding. Notice the circle around the tree.