>>29
That will definitely help if the problem is mojibake, but they'll still need a SJIS-compatible font. Changing character encoding and date styling options isn't going to somehow force a monospaced terminal emulator to become proportional-width, and most are decidedly fixed-width.

Off the top of my head, I only know of mlterm which can be proportional, although the DE ones like gnome-terminal can probably do it as well. Those would be a pain to set up within cygwin, though, what with all of the dependencies for a graphical program.