My dad is looking into recording his cassette tapes in the analog format onto his computer in the digital format.
What kinds of software/hardware will I need that I could do this on the cheap/free?
Also will the hardware/software change the quality of the tape for better or worse? And if worse on the cheap, what can I get for not too expensive for decent-good quality?
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Hardware is trickier: the most obvious thing you want to do is make sure your setup doesn't put any hum or noise into the system, so do some test recordings with blank cassettes.
A good way to check the quality of the recording would be to record some test tones onto blank tape (Google audio test tones) and then play them back and see what type of losses/distortions you're getting.
I suspect, provided the electrical grounding isn't messing with you, that most standard computer Line In circuits are more then adequate, given the source.