I hope my personal fight with this helps you too.
I totally got off track with pick stiffness. A more flexible pick DOES make it easier, however you need to balance the flexibility with ability to feel the pick for the practice I recommended. For play, then you want to go with what sounds the way you want. I grabbed three different variety packs from Dunlop back when I started. I progressed through using several of them, some only for a week or two, until I arrived at the orange one. If you are unsure of the pick stiffness you like (and it will probably change over time) then you would benefit from a reasonable variety. I linked the products here:
I do think that nylon vs steel strings will make your pick choice a bit different. I am playing steel strings on an electric, and have 4 electrics all with different physical profiles. My pick choice comes more from what I am playing (all strumming, power chord chugging, arpeggiated notes…) than from the guitar, but I do not have a nylon string to compare to.