There are several ways you could pace the rollout. Using your idea, you could try a small test file 'silent' copy as a test before the big one. Based on sucess or failure, put up a message and proceed or skip.You could put the candidate computer names in an INI file and check it with ReadProfileString. You could use the same file to log with WriteProfileString. Then pace the rollout by placing limited number of candidate machines in the file at a time.
You could do it all remotely from a central console, pushing out the file and initiating the install using the scheduler. This you could do after hours, providing you can get your users to leave their machines powered up.
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