Assuming he's filed a 27.0 steerer base down to 26.4 to fit an ISO crown race onto a fork designed for JIS, then yes, a file is the wrong tool. There's a good chance that the crown race, when fitted, will either not have the correct interference fit, or will be non-circular. In either case, you can expect accelerated headset wear and possibly difficulty in achieving the correct bearing preload to give minimal headset friction and minimal free play, leading to poor handling.
Assuming he's filed a 27.0 steerer base down to 26.4 to fit an ISO crown race onto a fork designed for JIS, then yes, a file is the wrong tool. There's a good chance that the crown race, when fitted, will either not have the correct interference fit, or will be non-circular. In either case, you can expect accelerated headset wear and possibly difficulty in achieving the correct bearing preload to give minimal headset friction and minimal free play, leading to poor handling.