Hi @de Fraine, Sean,
It seems that you have some sites that are still using the SharePoint 2010 experience, which is not compatible with the SharePoint 2016 farm. Run below powershell to check if all site collection are in the same version:
get-spsite
For example:
If there are sites with a collection compatibility level other than 15, run below script to upgrade
$webApps = Get-SPWebApplication -Identity "http://servername:12345/"
$sites = $webApps.Sites
foreach($site in $sites)
{Upgrade-SPSite -Identity $site -VersionUpgrade -Unthrottled $site.Dispose()}
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