Still, you learn things from experience. It's not as if you're entirely reinventing the wheel every time you start a new short story or novel. I would say that over time, a key thing I've learned about my own scribbling is that I use certain words with way too much frequency, particular words and expressions, and that when I go back and revise, I find myself cursing at myself dealing with these repetitions. You wonder how, without being aware of it, you can keep using the same words and constructions. It's easier than ever to find them now because you can use "Find" or "Control F", or whatever you prefer to call it, on your computer, but there are times I dread tapping "Ctrl" with "F" and a specific word since I know it will reveal to me the apparent skimpiness of my vocabulary and, worse, my lack of facility and inventiveness with language.
But that's where the learning from experience comes in. It's taken long enough, but now I've come to know which words and constructions I overuse. Here's a list I compiled when I was working on my last novel, Jack Waters - words and phrases I used with monotonous regularity and that took up a lot of time when I was editing:
in front of
nothing to do
Others you wonder what is it about your brain that you keep using them. Why do I keep writing "He started to" or "She began to" when I can just say what the person is doing.
But my point is that with time, you learn your own writing quirks. I've noticed that from book to book, I tend to keep overusing the same words and phrases. The sample from Jack Waters is not all that different from the words I overused (before revising) in the book before that. Now, at long last, I've become more pro-active and I'm on guard against myself, in first drafts, from overusing "start", "began", perhaps", "maybe", "one of", "almost", and so on. That awareness is a big help and means less revising of a certain type later. Naturally, I have to be on the lookout for other phrases I might come to overuse - one can never relax - but being on the lookout for them helps me find these repetitions faster than I used to when I was not so cognizant of them.
Does writing ever get any easier, even if you do it for years? No, I would say, not overall. But you can become aware of your tics and patterns and the habits you fall prey to unconsciously, and learn how to catch them before you slip into them and thus save yourself time and aggravation.