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Hope what I went through helps anyone who had the same issues. I'm subscribing to this guide's thread, so if anyone has similar problems to me I'll see your comments here and try and help. Otherwise, use Google and find some helpful Indian guy on YouTube that'll explain how to fix your problem.
Solution: What occurs is that within this software, achievements pop only upon closure of it. Turning off the PC before doing this, however, prevented the achievements from popping upon closure of the software as I never technically closed it before turning off the PC. It was only clientside, and didn't translate server-side. So, I simply launched the VM again (painfully slowly), launched the software again, and made sure to close out the software BEFORE shutting down the VM.