Sorry for the lack of response here. I was able to figure out the issue and it is the same issue described in this post: NTP (chrony) not starting on newly provisioned device - #10 by nebbles.
By default it looks like it is indeed required that the openbalena backend be up and running in order for ntp to work correctly. On our devices we saw the same behavior as in that post, but the error occurred because our openbalena server was down. Basically, the timesync-https service just keeps making calls to “[apiEndpoint]/connectivity-check” forever if it can’t connect and chronyd.service is waiting on that service to complete/exit before it will startup. We aren’t yet certain how we will work around this behavior. It would be nice to just be able to disable the timesync-https service, but I don’t believe that is possible?