I want to apologize for the delay in response. Right after posting this I got slammed at work. Yesterday was the first good office day where I could sit down and get this sorted.
I took the lazy route to olivierlambert's suggestion and just made a new XOA VM. I successfully important a 1TB Windows 10 VM last night, so the issue seems resolved.
I'm somewhat confused by the version numbers I'm seeing, which I'll post below, but everything is working so I can live with it.
Non-Functional XO
xo-server 5.93.1
xo-web 5.96.0
Functional XO
xo-server 5.80.0
xo-web 5.84.0