Well,
After a couple of hours playing around and trying to get my levels right one thing is clear; the "out of the box" experience that I get with my Toshiba notebook as a recording studio leaves much to be desired.
The original setup was essentially to run the line out from my practice amp into the mic input of the notebook.
That would have been the easiest from the standpoint of recording one track, then playing it back in the monitor while recording another.