Re: Did I do some damage?
Ok, something isn't quite right here;
You say the leak is most severe at speed, yet the boot is out of the water then. If the boot is split, you have a second leak as well.
As for the screws that are turning freely, pull them out, dip several wooden toothpicks in marine glue and fill the holes with them. Let the glue set, then cut the toothpicks off flush. Drill a tiny hole in the middle for a guide, then run a screw in. When you mount the new boot, squirt some sealant into the screw holes as well. Water slowly seeping past a screw will rot the plywood.
The factory screws are stainless #8, 1?" long. You may want to get some longer ones. The transom is 2" thick