You can clock into more than one job at a time and the time will be divided between the jobs (if you resource group settings are correct). So the set-up guy would have to clock into the 10 different jobs.
The mass clocking in/out can be handled with the work queue (try this first) or UI customization on a dashboard.
I can’t remember exactly what each check box does (so make sure you test), because once we had them correct to our business, we didn’t mess with them, but the split burden, and burden = labor has to be set correctly or else it will think you are running multiple machines if you are clocked into multiple ops.
See this thread for some discussion about those settings.