Hey Zach - since I live & breathe IT for a career - what is the issue you keep having with the upgrade? I would like to suggest you break down the upgrade into multiple smaller chunks and deploy each one in succession once the prior one is working.Basically I tried to update to a newer version of the software we use ( Oxwall ) and it corrupted the site. Our host does auto backups so we reverted to the last known most recent file. Other than that I am not sure what happened nor why.