Can rsync transfer security/ownership information between two windows machines ?

cwRsync itself has no support for it. However, after an rsync operation, you can use Robocopy (standard in more recent Windows versions), to transfer all windows specific file information (NTFS security, timestamps, attributes, ownership, auditing info):

ROBOCOPY source destination /XO /XN /XC /E /COPY:ATSOU


options /XO (exclude older), /XN (exclude newer) and /XC (exclude changed) assure that only existing files are targeted. Option /E is for recursive directory operation including empty ones. Option /COPY:ATSOU instructs Robocopy to copy only attributes (A), timestamps (T), NTFS security information (S), Ownership O) and auditing (U).

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