Unable to boot - share your thoughts

Im pretty sure when boot hits a wall, there are no iterative messages. Maybe boot-info could disclose, but not everyone has the nouce to delve that deep; os should not be counter intuitive, but full of onerror logical feedback at the very least.
A typical example would be HERE. Clearly a bit more logic in the boot process would enable the user to either sort or get a more intuitive feedback.

It would be interesting to see how Windows 10 boot errors and feedback if any compare to Linux.