I'm not sure why writing for others became harder. Probably a reluctance to give away anything you might conceivably use yourself caused a block. I did it, but it remained hard when it had once been easy.
The trick to writing for people is, you have to be able to turn them on in your head. And know how they'd word something or how they'd inflect it.
I think I'd be pretty easy to write for.
I haven't ever found any great writing on that wonderful and often unappreciated art form, the insult.