What’s the Best Strategy for Resetting Windows and Mac Laptops in a Rental Setup?

You're looking at two different workflows that seem integrated but can be tricky. Windows has some good tools (like MDT/SCCM if you're really going in-depth), whereas managing Mac devices can be quite the headache. For Office licensing without user logins, consider using shared computer activation for Windows and volume licensing for Mac. You could deploy that using a script to install everything smoothly without future headaches.

For a mixed fleet approach, you really need a strong Mobile Device Management (MDM) strategy to handle the wiping and resetting natively. For Windows, Autopilot paired with Intune would be a great choice. You can set it to operate in 'Self-Deploying' mode since you don't have fixed users. Intune also offers a quick 'Wipe' command to get the devices back to their Out-of-Box Experience (OOBE). For Mac, linking Apple Business Manager with an MDM like Jamf Pro or alternatives like Mosyle could work really well. It’ll allow you to enforce the MDM profile even after a wipe.

You could definitely reimage them, but remember, you'll need to keep the image updated for security patches. We used a product called Deep Freeze for our training devices, which allowed us to take a snapshot of the system. Any changes made during use would revert back to our original image, including all installed software. I'm not completely sure about Mac compatibility, but Deep Freeze does advertise support for it. When it came to applying security updates, we periodically updated the image and then saved that as the new frozen state.

I think you should check the licensing for Microsoft Office. Whether it's a subscription or a one-time license, technically you're 'reselling' the software when clients use the laptops. However, if these laptops are fully owned by you and only used for events, it sounds more like short-term rentals which could be fine under the licensing agreement. Just make sure that you're compliant with Microsoft's terms.