I have Git for Windows and "less" from GNUWin32 installed so use "less" as my pager. The GNUWin32 version handles Windows better than the Git for Windows "less" version. In any case, PerlDoc doesn't work well with it, so my fix:

# Perldoc paging using less:
create:
c:\strawberry\perl\bin\perldoc
  (without extension)

Then, in Pod::Perldoc
  search for "-R" and comment out or put an if {} around, e.g.,

if ( $^O ne 'MSWin32' ) { 
    BLOCK
}
[download]

My problem stemmed from a command line option to "less" that my "less.exe" didn't support, so it was just printing the whole POD at once with an error as well. Now, 'perldoc ARG' produces the PerlDoc for "ARG" (whatever it may be) using the "less" pager.

Hope that helps.