Personal Context: I am tech savvy, but in a dev sort of way, weak on the admin side. Apologies for missing details.
I have a virtual server running Windows Server 2003 R2. I have sshd running via cygwin. I have a directory (itself containing many nested directories) that I want to set up so that a particular user group will always have full control over any of the files within, irrespective of the individual file permissions, but I do not want to make the the users Administrators. The access is likely to be via sftp/ssh but I think that will be handled automatically as long as the file system permissions are correct. I have tried giving access at the top level folder to the group and even doing the "replace all child permissions" option, but this only handles it for the files currently present and not for new ones (and caused issues of it's own).
If this is something far easier to deal with in Server 2008 that is good information as we are likely to be migrating in coming months.