Solutions
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SerpentMage's post in New Server Boots to "GNU GRUB version 2.06" GRUB prompt was marked as the answerSo I think I fixed it? I got a different USB drive, created a new boot drive and it worked. Odd thing is, I did this same thing earlier with this same drive. I'll admit I very possibly messed something up and/or got the USB drives mixed up. I was doing this while working earlier today.
So yeah, sorry for the false alarm. Thanks for trying to help trurl!
-Serp