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We are trying to upgrade several servers running Windows Server 2012R2 to Windows Server 2019 running in VMWARE environment and we get a sysprep error when the machine reboots then an error that says it's unable to configure device and then undoes the changes. I have attached screenshots, hopefully someone can help me. 
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No worries, I'd suggest starting a case here with product support.
https://support.serviceshub.microsoft.com/supportforbusiness
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What roles are installed? Might check the $WINDOWS.~BT\Sources\Panther\setupact.log for more details.
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It is a print sever, so it has the print services role installed, but we had the same issue with a file server and a web server. It has only worked on one server at this point and that server was a file server that handled the Home Folders
Here is the setup log if it helps find a resolution
Debugging windows setup files is beyond scope of forums support. Some info here.
https://learn.microsoft.com/en-us/windows-hardware/manufacture/desktop/windows-setup-log-files-and-event-logs
https://learn.microsoft.com/en-us/windows-hardware/manufacture/desktop/deployment-troubleshooting-and-log-files
If you needed assistance with debugging you can start a case here with product support.
https://support.serviceshub.microsoft.com/supportforbusiness
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In-place upgrades can be iffy for any number of reasons and are never recommended. Time may be better spent standing up a new one, patch fully then migrate the roles over to it. You'll also end up with a cleaner installation.
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I have done that with these servers, but we have several servers that run a proprietary software that we really don't have the option to stand up new servers.
Compared to in-upgrade we suggest to do a fresh installation of Windows Server 2019, then migrate your roles and data.
In fact, since Windows Server 2016 released, upgrade processes are essentially a clean-install then migrate data.
I know you don’t want to clean install server 2019 because of the proprietary software, but this proprietary software may be the cause of in-place upgrade failure.
For current situation, you’d better open a request ticket with Microsoft to do a deep research on this upgrade issue, hope you could make it.
https://support.serviceshub.microsoft.com/supportforbusiness
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Any progress or updates?
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No, progress. My boss is adamite that I try to fix the problem as the company will charge thousands of dollars to come in and reconfigure new servers. He really wants to do the upgrade. I explained that is not the best course but he still wants to try. He thinks even if I am able to successfully do half of them that is better than none.