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I'm pretty sure that the guys with the biggest vibrato (Stochelo, Jimmy) can only get that feel with lower tension (light gauge) strings. And I believe that they use the silk and steel 10s.
I think that the lower tension of gypsy jazz guitars (as compared to flattops) is much more suitable for the rest stroke technique because of the wobbly pick grip. softer responding strings just "feel better" with rest stroke. i also think high tension is really good for alternating picking style.