Roger Waters' picking technique is entirely different from Carol Kaye's. Barely on the same planet.
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When I was just starting out back in the stone age, there was no internet, no MTV, no Bass Player magazine. What we did have was Guitar Player magazine, which had a column written by Carol Kaye. I learned a lot from those columns including proper left hand technique, but probably the biggest thing was her use of the pick. I had started out playing with my fingers, but began to incorporate using a pick in my playing. Unlike today where there seems to be some kind of stigma attached to using a pick by some people, they were lots of respected players using a pick. Maybe because I didn't know any better, I just played both ways. If I was playing a tune where the original guy played fingerstyle, that's what I'd do and if they'd used a pick on the record, then that's what I'd do.
As a lot of folks have pointed out, Carol Kaye is a great resource for learning to play with a pick. She always used flats with a hard pick and also played pretty hard. Based on recent videos, she still does.
Based on my own experience, unless you are going for a sound like Chris Squire or Live-at-Leeds-era John Entwistle, flats are perfectly fine with a pick. Pick selection is very personal and it sounds like you are trying a lot of different shapes and thickness, which is what you need to be doing. I like a little flex in the pick, but some people like them perfectly stiff. Good news is that finding the right pick is probably the cheapest gear investment any of us will ever make.
While you are getting your technique together I would recommend you practice using different pick directions: all down strokes, all up, alternating, sweep, etc. Eventually when you are playing the tunes you will naturally gravitate to the technique you need for the song you're playing.
There are a couple of little things that I never really appreciated until I had been playing with a pick for a long time. These may sound dumb or insignificant to some people, but I've found that spending some time focusing on them was very beneficial to me. First off is learning to hit the string with the pick flat against it rather than at an angle and with the pick perpendicular to the top of the bass. I've found that you have better control that way and you can always vary the angle of the pick for a different tone, which I do sometimes. Also be cognizant of how much of the tip of the pick you are using. You don't need much to get a good sound and, generally speaking, the less you use the faster you can be ready to strike again. OTOH there are tones you really can't get unless you dig in and use a lot of the pick, though that can tend to slow you down. The idea is to just to realize that you have options and find what works for you.
Hope this helps.
Make sure your right AND left hand muting chops are on point, too so you can calm the tone down when needed.