On Apr 28, 2:56*am, Senin wrote:
I am having my house exterior painted. *Full paint job, I even paid
extra for his handyman/carpenter to replace dryrotted planks on my
wood siding.

My question is...

Should part of his job be to countersink the nails that are exposed on
the siding?

*IF* you can argue that 'counter sinking nail heads' is included as
part of a standard methodology for an expected high quality paint job;
go for it.