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The better looking the source, the better looking the video....but there are considerations.
Use your eyes to judge. If the tape was recorded on a standard 2 head VHS recorder, popping for a 4 head S-VHS isn't going to improve the picture much (though 4 head S-VHS's are quite cheap nowadays) if any. While the S-VHS is a higher quality output, it can't improve a poor tape.
When converting VHS to digital, I'm more concerned with how smoothly and quickly the VCR I'm using responds to it's controls which is why I use my old Sharp VHS SlimCam as my tape input when I convert.
One other suggestion, always clean your heads on your playback VCR and fully fast forward/rewind the tape before playback when converting video (to have the smoothest/cleanest playback possible), nothing is worse than capturing snow, tracking errors, or a tape slip on baby's first steps....and then having to do it again.
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