In article .com,
Greg Copeland wrote:

My brother is a CFI, training Apache Long Bow pilots and would like to
transition to GA after he retires. Was wondering if anyone knows of
any books which will help prepare a career military helicopter pilot
for the world of civilian, fixed wing aviation? Specifically,
anything that covers transition to FAA private pilot, complex
endorcement, and IFR certificate.

I have not been in that situation, but those who have tell me to get the
certificates from the FAA before they separate from the military. Have
him contact the nearest FSDO and talk to them about what they want in
the way of documentation.