How do I ensure permissions I set apply to all files and folder below

Hi Everyone,
I dont know if you will be able to help but Im sure someone will know the answer to this one.
OK, so, I run my MAC with a VMWare Fusion Windows Virtual Machine running Windows 7  and I manage my time machine and some other backups using a Netgear ReadyNAS NV+.
What I am finding irritating is that say I use the Apple+CTRL+i command to change the permissions on the 'Pictures' folder to give the account I use for the Windows access and ReadyNAS access to have 'Read + Write' permissions, then 'apply to enclosed items', this works fine.
However, should I move files, create new ones or the system creates new ones, it does not apply the permissions I set. This is irritating because it is preventing the NAS box from completing a sucessful backup and I often find that if I try and open an image for example on my Windows VM, I will get a messaging informing me that I don't have permission to open that file.
What I then have to do is repeat the permissions setting process, then I can open the file and work on it.
This is becomming extraordinarily irritating and Im sure there is something I can do but I dont know what that may be.
PLEASE can someone help me from going insane!?
Thanks,
Ross

When you create an action, the first step is the "Start with" step where you can select a folder. Just to the right of that there's an icon that you can click to select other file types. Just deselect them all.
An alternative it to temporarily move the PDFs to another folder.

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