Hi Jay. I'm Greg, an installation specialist, 10 year Windows MVP, and Volunteer Moderator. If you will work with me I will be here to help until the issue is resolved.
The WIndows Upgrade assistant is buggy. I would manually upgrade to the latest version 1909 by opening the Media Creation Tool from this link:
http://windows.microsoft.com/en-us/windows-10/m..., choose Download Tool Now, then open the tool and choose Upgrade This PC Now. This saves your files, apps and most settings in place, is the most stable method to change versions, brings your Updates current, resolves most problems.
If any problems report back the verbatim error and number, then continue with these steps for overcoming Version Upgrade problems:
http://answers.microsoft.com/en-us/windows/wiki...
If the Version has problems I will work with you to try to resolve them. If the problems are unfixable for now, you have ten days to roll it back in Recovery settings. You can then hide it so it doesn't try to reinstall following this same method:
https://www.howtogeek.com/223864/how-to-uninsta...
Most problems are resolved by doing this gold standard Clean Install which should get you past all difficulties as it has millions of others who have followed the steps in this link and never come back to report another problem:
http://answers.microsoft.com/en-us/windows/wiki... . So read it over and see if its something you want to learn to do.
I hope this helps. Feel free to ask back any questions and keep me posted. If you will wait to rate my post, I will keep working with you until it's resolved.
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