Dont even think of Utilising Win2K. Its slow and far too memory hungry for its own good. WindowsXP isthe way to go as it retains the speed of Win98 and more compatable with games then 2k.
sure XP looks like ####, which is why they included the windows classic interface to make it even faster and nicer
now to the real point of the thread. whdload should install just fine if youve setup a bootable Harddrive Workbench. Its probably best if you install it on a real Amiga and then simply trasfer the installed game over.