Foolio,
I play everything on nylon string guitars. For the blues, get a flamenco setup (not classical)... low and fast, as loud as you can find, punchy sound with not a lot of sustain.
I recently got my first steel string... very nice guitar (Eastman E10P), but I'm still trying to decide if I like it or not. The best thing about it is that when playing with others who have steel strings I can now be heard. My fingers definitely prefer nylon strings and wider necks!
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