I would doubt that the iso is an issue. Unless @bendurham441 has loads of bandwidth and downloading a 500MB ISO is a snap, I’d hold off on that. (Of course, one could download it on another system while following other leads, that’s not a terrible idea).
Getting messages about files not being found… I suspect you’re getting them at the stages where something is being performed on the target partition, which relies on data that should be on that partition.
That would mean things aren’t getting copied over.
Now, I actually do recall something like this happening to me, when I was playing with things for documentation purposes a couple of months ago.
I had a VM, and I was using a 2.5-inch IDE HDD on a USB bridge, which I’d given to the VM. I did run into various things failing, and they seemed to be due to missing components on the target partition. Suspecting the disk was wonky, I eventually used a virtual disk (file on my host system) and the problems ceased.
I’ve yet to get back to testing that disk (it’s just one of a handful of spares I keep lying around with no good use for), and I don’t know whether the disk itself is to blame, or whether something just wasn’t being handled correctly. Having been on a USB2-IDE bridge, the OS doesn’t get to talk directly to the disk in the same way as it would were it on a native bus…
Things like cache flushing/delayed-write problems come to mind; however, I’d normally expect failures in that area to cause the system to detect an error; in this case, that doesn’t appear to occur.
If anyone has any experience with those sorts of problems, they might have information worth exploring. Maybe some settings that can be played with, that are available via commands on the live image (mount options being the likeliest)?