What I think I do is to relate any new material to how similar it is to something else. The closest that I can come up with something that's already in my experience, the easier it becomes. All I have to do then is remember where it differs, like relating a chord sequence that comes from some other tune, or several different tunes, or maybe parts of them and then work it from there.
... by then I was getting a little work, doing some playing and getting paid for it, not very much, but enough for me to feel justified in buying a real instrument. I bought a Gretsch with a De-Armond pickup on it and a second-hand Gibson amplifier; it looked like the one Charlie Christian used. I guess it was the same, although there were several models coming out at that time - this would be in I939.
The result was the same as tuning down the strings by a semitone and using a capo at the first fret. With less tension in the strings, the sound was more mellow and softer; it also allowed me to cover a larger span of the fingerboard. I used this for quite a few years, but eventually I went back to the standard fingerboard.
