No, not much downward pressure on the screwdriver when reusing holes, only when screwing into fresh holes because that's when you're cutting the threads into the ski. When reusing holes you'll be reusing the threads that are already cut. Best to set up your screws like normal so that they're protruding from the binding baseplate just 1-2mm then sit it in place. Push down a little on the screwdriver while turning it backwards (unscrewing, counter-clockwise). You should hear and feel a click once per rotation when the ski thread and screw thread line up. Just after you feel that click on a backward rotation screw it in normally and slowly without much downward pressure and you're gold.
Woof glue, epoxy, whatever you want. I've had no issues with either on several remounts into the same holes. Just go easy with the final tightening especially if it's a non-metal ski; it's easy to overtighten and strip the holes.