I've had issues with the OSX clients in the past, this has because a host-based antivirus/firewall was stopping cloud communications with the device, If you have a host-based firewall/antivirus ensure that you set a policy to allow connectivity to the required IP's (help>Firewall info).
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If it isn't in the Meraki profile settings, another thing to try is a soft reset on iPads that show this error. (Turn off the iPad, then restart it, and as soon as the Apple logo appears, hold the power key and home key both down until the apple disappears and then reappears again.) It seems I have to do this on almost every iPad with iOS 10 or higher (which is most of them now).
In my case, they are checked, but still I see in the user config as location disable.
On device, app was allowed to track location all the time in privacy.
User dashboard always show "approx" location using IP on most of the device... years ago I fixed that problem using Apple ID and register device with find my friend, disable modification of account, and that was the only reliable way to really track device, Apple FMF work every time.
But it's more complicate to setup... and it will be useful to be able to track device from Chrome, not another ios Device.