Hey Tommy! So I usually try not to print black on a black shirt. There have been times where I’ve used it to trap colors that were causing some fine details to disappear like line work but I try to avoid it. So I used to just use color range to select those colors and get them onto their own channels and I wasnt very good at it until I saw this video by Rising Sun. I seriously cant think of a better explanation of how to get really accurate greyscale separations. This is the video that helped me and its an awesome view:
I lighter one is better, it will just be a great to print even on darkest t-shirt. Try check this anyway http://www.digitekprinting.com/ if something is night right then will give you fixes right away.