So after resetting the PC overnight, I was able to download and install all 99 important updates. I thought I was in the clear.
My system restarted, and then went to the configuring updates screen. I let it be for a while, it's been a 2.5hr process so far from download to configuring. I just looked at the screen again and it now says
"Failure configuring Windows updates
Do not turn off your computer."
I have never had so much trouble with a brand new computer. I am so, so frustrated. I really hope someone has some insight or guidance on this topic...
Very frustrating! We have been deploying mass amounts of computers and ran into very similar issues. You have a ton of updates and deploy them only to have the computer hangup and revert changes back. It becomes a nightmare to try to get it into a ready-state.
Ultimately, we ended up using a fully patched image to deploy to the machines because of problematic factory images. In this situation it was with Lenovo computers. For you however, this is most likely not an option.
I would recommend installing the updates in stages. Install anything .NET related and then restart, then do another set of updates based on the description in Windows Update. This will take awhile but at least the update will be applied and let you update successfully. Assuming you still have KB2938459 pending - install that one last.
I believe the main issue here is that components are updating and other updates are related to it and it causes a problem when trying to actually apply a second update. By staging out your updates so that you can restart after blocks of 10-20 patches it should be a big help to get this fully updated so that you can install 8.1. Sorry this is so troublesome but the computer itself is probably fine and it is just the combination of OS Image and bulk Windows updates.