“The last Windows that would boot to a prompt was Win 98SE.”
LOL. You are so wrong. All Windows versions can boot to command prompt. Here is example for Vista (see method 2): http://www.vistax64.com/tutorials/67612-check-disk-chkdsk.html
I think you are mixing up booting, and switching to.
If windows is down, you cannot get to a dos prompt in anything since 98. (although you can use various universal recovery disks)