I think for me it was a gradual learning process.
It is easy to catch small bass. You can always toss out a rod with a clam on it. This will keep you from getting skunked on a lot of trips, and guys may use this as a crutch. I know I did.
Then you see that guys are getting bigger bass by matching the hatch with artificials. When there are big bunker, they will throw a pencil popper which mimics the splashing behavior.
When the bait is peanut bunker or mullert you learn that you can throw a swimmer that has that profile. If you figure it out right, you start getting larger fish.
There is nothing like the thrill of catching a 30lb bass in the middle of the night, on a plug that so closely resembles what they are eating that they inhale it and almost pull the rod out of your hands.
As I said, it took me a while to get to that stage, and I used bait as a security blanket. I still do when it's cold, or there is a certain condition to the water that makes throwing that bait worthwhile
ie. eels in cold water.
I was helped along the way by the old salts or sharpies you mentioned. They saw me trying, and threw out a tidbit of advice at a time. I did struggle for awhile to get bigger fish.
I learned that you need to pay attention to tide stage, read the water, and mark that structure.
I learned that if a guy fishes an area and thinks it's dead, it's possible he could be fishing the wrong time.
All that comes together, but as you said, you need to put in your time to see it for yourself. Good thread, dark.