Skeeter, first of all thanks for responding.
I just tried that and had two completely different results. I'm using the pen on paper to test to not waste any more vinyl. I put my sheet of paper in, put it to where there was about 1" past where the pen would touch down. I loaded the design (4in x 5in) and pressed "Cutter" to bring up the cut screen. Before pressing cut, I pressed "Origin" on the cutter itself. That presses the pen down. I then hit cut on the software and it barely fed the paper at all and did the "cut" great. I tried the exact same thing again, same placements etc and it fed the paper backwards too far and it fell out of the cutter. Same design, same steps. This is what's frustrating me.
Also, I have no idea what a Tripp-lite Keyspan Adapter is but I'll google it. I never used to have this issue of it feeding what seems like random directions / distances before cutting. I'm going to keep trying on paper until I figure it out.