this is a great forum. I have already learned alot. Who doesn't love a type of music that looks like math?
A lot of players probably think being obsessed (if that is the right word) about picks is silly, but it can be important I think. I spent about (cough) 10 years looking for THE pick. What did Mclaughlin use? Burrel? whoever. So I would try this and that. I chose to blame the pick for lack of technique. why not?
Butfor me i learned a few lessons. One was, if you are playing different types of music (strumming vs single not fast stuff), you have to find a pick that is a good compromise between the two (unless you have great technique). For me I decided since George Benson, Robert Fripp (pre GC) & Kenny Burrell can get away with a medium pick, so can i. But for single note soloing, its the dunlap Jazz III 208. its bigger so i can hold it. As much as i tried to use those little fender "jazz" picks, forget it. Of course when you use light strings a harder pick is harder on the strings and strumming takes more concentration. The silly thing i discovered is the JAZZ III gave me alot more speed, but I wound up only playing the scales/riffs i knew. no creativity. Lack of practice at that speed i am sure.
And of course the sound of a pick. I was trying a version of Emily Remlers Afro Blue. didn't matter which guitar I used, just too bright or something. Started playing with my thumb mostly (I guess there is a jazz legend who did that...whatz his name?

) and a whole new world opened, instant tone i wanted....no pick...who knew? Course if you do anything faster you will eventually have to use hammer-ons, but i'd rather have tone and some originality vs. a sterile stiff scale.
OMG...i've bored myself! But I hope someone experimenting will find this useful. Course there are *TONS* of posts on this on the various forums. I know, i read them all.

You can spend your life doing that. Course now I read all the posts on soloing over II-V-I's.
Jay