Repetitive copy of Win10 OS to VM

We will be repetitively copying a Win10 OEM license environment on a Dell computer to a VMWare image running on Workstation Player 15 on Linux.  The updated image will replace the earlier image over time.  We understand we must purchase an additional retail OS license to run the VM image. 

Two questions please.  Will we run into problems with a single retail license as the VM is replaced (using the same host hardware)?  Is the same situation true if we were to run the VM on Fusion on a Mac, instead of Workstation Player on Linux?

Thank you, Ron

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