Booting from a DVD shouldn't really be a problem. If you're certain that your system recognises both of your hard drives and optical drive, then I can't really imagine anything else than the DVD itself being faulty.
What I find suspicious about that initial screenshot you posted, is that it suggests you need to repair your Windows configuration, but according to what you're saying, there's nothing installed currently. Faulty DVD sounds very likely in fact.
You could test the DVD in another computer, though I wouldn't be surprised if the DVD works fine if a Windows installation is detected.
edit: vvv oh yeah, a CD-ROM drive won't read a DVD, but then most people call them CD-ROM drives, regardless of what they can actually read. Which is silly.
By the way what I said earlier about bootloaders is just what I've learned through personal experience with dualboots. Things can get messy if the Windows bootloader tries to override the Linux one. Then again, this was back in version 6 of Ubuntu or so. Things may have changed.
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