Updating from version 1.6.1 to current on child theme

I am in the process of updating a website from 1.6.1 to the current version. The website is using a child theme and after updating a staging site to the new theme by overwriting the parent theme folder, I lose all my styling, page content, and lots of other things. I realize it's a big jump to go from a heavily customized old version to the current. Any ideas or tips to get it updated properly?

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