I already have code that will enum a folder of hotfixes and parse the reg comparing them to installed patches.

at that point, I'll have robocopy copythem to the client machine. Once the copy is complete, I'll pester the user at 5-15 minute intervals to allow the install to happen, "A system update is available, do you wish to install now?" Then "Update is complete, Do you wish to reboot now?" and then robocopy would copy the next file if available?
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How to ask questions the smart way <-----------> Before you ask