I have modified a press and attached a Jacobs drill chuck to it to use with the diamond awl. It also works very well for punching the holes for belts, chicago screws, and installing snaps. For making the 2 layer belts and holsters, I don't have much of an issue on keeping the leather on the table portion just using finger pressure. I did take a 2x4 and cut/glue a piece of scrap on it that I can use as a foot if I have some tough sections. I am actually using a cheap plastic cutting board under it that is working out well as a temporary table until I can make a thin metal adjustable table that will be adjusted to use as a guide for faster punching stitching holes.
My advice is buy a bigger arbor press to have more clearance.