Hi JeremyEnjaynes,
My name is Darren; an Independent Consultant, I'm here to help you with your problem.
Firstly, please try running the troubleshooter:
Go to Start > Settings > Update & Security > Select troubleshoot tab > under "get up and running", click on windows update > click on run the troubleshooter and follow on-screen directions.
Next, please follow the steps on this guide to reset windows update and try updating again (Take note that you will need to run the command prompt as an administrator):
https://docs.microsoft.com/en-us/windows/deploy...
However, if the issue still persists, you can try using Windows Media Creation Tool to update your pc. (There is an option to keep all files and apps)
Please refer to the following link and click on download tool now under "Create Windows 10 installation media":
https://www.microsoft.com/en-us/software-downlo...
After download, run the Media Creation Tool then select "upgrade this pc now" and click on next. It will download the latest window and then install it. But before installation, it will allow you to choose between keep all files and apps, keep all apps only or clean installation.
I hope this helps. If this is not exactly what you need, please explain more so that I can help you better.
Thanks