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A point for dropping to Eb is that it gives you open strings which have sustain. The style of jazz accompaniment, as epitomized by Freddie Green, is closed and muted strings all over the neck, on archtop guitars that are notable for the punchy attack but minimal sustain, so the benefit you get is being on the position marker rather than off it. I don't doubt ...

Tuning to Eb can have a variety of advantages. When playing in a band with horns that are Eb and Bb instruments, tuning to Eb means that you use bar chords and play in their key much more easily. Having that lower Eb also means that for a tune in that key, you don't have to go up almost a whole octave to play the root note. It will also change the tone, ...