Interesting responses. Seems like one of the above suggestions would be a very nice addition to be recommended to the author.
Well, my own 2 cents and not so elegant.. I once looked at a tool that would give you a virtual unix filesystem packed into one windows file. Posted it here somewhere.. ah, here I was asking about PAR and gui app bundling tools, and found Thinstall. It's not free and maybe not what you want, that is you might as well use cygwin I would guess then.
Of course you could also just build to a local folder on unix and then write a small utility to copy while renaming onto your usb stick. That way you don't have to recompile just to get the files renamed. Would this be sufficient? Of course if you actually want to run these on windows then you probably want to compile them for windows if they are not PurePerl but anyway..
Um, also I don't mean to be silly but I wonder if perhaps you just tar the files up then a windows untar utility might even rename them for you? Apparently this is not uncommon, I looked and found on the net Michael Husted's freeware untar. So maybe you could just tar up your man pages folder and untar it on windows. Well anyway here it is. Of course it would be nice if MM just did what you need but here's the info for this sort of meta-weasling away from the problem.
Untar v1.14 Description:
unpacks TAR (Tape ARchives) files often used in Unix and Linux systems
+. Subdirectories and illegal characters in file names (due to differe
+nt file name formats between DOS and Unix) can be automatically handl
+ed by the program.
Untar also supports long file names at the DOS-prompt of Windows 95/98
+/NT by renaming the files after untaring them.