#1
I have a Fender MIM strat with stock pups, and a Fender Blues Delux Reissue. I was wondering what wold be a good new set of pick up when the configuration is SSH. I play alot of blues, psychedellic, funk, folk rock, lsd induced sounds, and a little punk.
#2
california specials
Guitars:
Ibanez IC300
Fender American Strat w/RioGrande texas specials

Amps:
Fender FM212R
a now broken tube amp

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#3
You could get away with the genres with a set of Seymour Duncan SSL-2's in the neck and middle, be sure to get the middle one RWRP...The single coils will get you blues, psychadelic, funk, and folk.
And then for the bridge...SH-14 Custom 5 is a good pickup that I think is pretty versatile. It should be able to do blues, punk, and psychadelic rock. Check out clips on their website, seymourduncan.com.
#5
Oh, absolutely. I love it when people say that. A humbucker will never be able to truely replicate single coil tone.

Just buy a new pickguard.
stewmac.com has several different SSS options.

And then just buy a slightly hotter bridge pickup...like...maybe an SSL-4, if you're looking for hotter single coil tone, or the SSL52-1b, for a nice tight bottom end for the bass strings, while retaining that glassy tone on the treble strings.