Its a ground switch signal so I would get wiring etc that is big enough to run the light, all the computer cares about is that the terminal is grounded. Most of that stuff is less than 5 amps. Any size will work so long as its big enough to run the light....
The other/best option would be to run a relay, and split the ground signal so that the computer gets a signal and the other leg trips a relay that would either turn on a light or turn on the switches light... This will make it so that there is no noise on the ground line to the computer (they are pretty tolerant already though....)
If you went the other route with two switches in parallel, I would set it up so that when the shifter is in high the button is depressed once moved from the high position it ohm's to ground... Would be very simple to setup, however all of your time would be spent building the brackets. If you did go this route build the brackets off of the trans etc so that it can twist with the drive train under load... I would go this route, even though it would technically only be for the high-low portion of your crawl box and t-case I would have a light that said 4wd on the dash...