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Part 1: Yes, you should be able to enable a script setting via a group policy object. Manually specifying it in the User Property sheet is recommended as a troubleshooting step.
Part 2: By default, logon scripts run as a background tasks. As a troubleshooting step, you can try using the Start.exe command-line tool to run local and domain logon scripts as a foreground process, as explained in MS KB article 265016, How to run a domain logon script in the foreground with the Start.exe command-line tool.
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