I took a few lessons with Rodney Jones when I moved to NYC in 1995, and he picks with the 90 degree angle, which he got from Benson. He gave me a series of technical riddles to figure out, which helped me switch my hand into that position. For me, it's incredibly relaxed and gets the best tone, because it's impossible to "overplay the string" - which is that "pingy" sound, that I, personally can't stand on a guitar. The 90 degree attack lets the string ring to it's truest vibration, the lighter the touch, the faster you can play, and the more dynamic you have to work with, articulation-wise.
Always practice with an amp - if you don't, you will pick to heavy-handed. The amp and your guitar together are your instrument, so if you practice, listening to yourself through the amp, you'll develop the right touch for your desired tone.
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