Third would be more verbose reporting information in grub, to say why it couldn't recognize a disk with a correct partition number. Fourth would be better reporting in Windows to say why things failed - that is, an equivalent to the system log under unix. Hmm, I bet there is, but I just don't know how to find it. There's probably more, but that's enough for now. Don Norman is right.
Computers are still in their primitive infancy.
Don't come back telling my why things have to be done this way. Think of it as a challenge. People use software to achieve goals in their domains. Bear in mind too that I've been a programmer since '83 and a professional programmer since '95. I'm not the only one who hates them.