6) Is this all pointless because the R2R no longer works, and the tapes are in poor condition, and will jam/flake off into the R2R even if the R2R starts playing them?
5) Do I need some kind of hardware in-between the R2R and the laptop, or can I just plug in something on both ends, and run audacity once I figure out how to use it?
3) There's a headphone jack out, not sure if it's 1/4 inch, or 1/8 inch, and I don't know its impedance, and I don't know what other outputs there are. Maybe a line out?
1) The R2R is thick tape, but too thick. Maybe double the width of a cassette tape, as best I recall.
I am aware of audacity, though I've not used it.