How to share a folder including all elements?

I am setting up a synchronization routine from a Windows PC and the iMac, both connected to the same LAN. To do this, if I have a folder that on its turn contains other files and subfolders in theory for that main folder I should select "Apply to all elements included" option in the information panel.
My current problem however is that this is not working, i.e. I have to apply this setting to all single subfolders and even root files for the main folder.
Am I perhaps missing a particular global setting?
Thanks in advance

Although I have purchased an iMac, my main computers are still PCs and the situation will stay so until the iMac is ready to become my main working computer. Further, I am running W7 under Parallels and are synchronizing to the iMac side all Windows documents so that I can use them with that very W7.
The problem occurs when I try to synchronize some of these Windows files with the iMac's Document folder for a certain application (Windows mail application in this case). I am not sharing system files (and none of those files are locked), only mail data files and this operation just goes well when I do the same type of synchronization between all other Windows PCs.
However a few minutes ago I tried to synchronize other Windows application's large folders with multiple-level subfolders (mostly Word, Excel and PDF files) and it went just fine. So may I presume at this point that this is the 'apply to enclosed items" bug in snow leopard you were mentioning?
Kind regards

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