Personally, I’d have to say the best it’s been was either the early 80s or early 90s.
In the early 80s, there was magic in watching the original movies in theaters or catching them on HBO at friends’ houses (we didn’t have cable until the late 80s), or whichever of the three major networks might have been airing them on their movie night. And, obviously, the action figures were fun.
In the early 90s, we had access to the original films on tape, LucasArts games, Dark Horse comics, the novels. None of the supplemental content from that time period was better than the films, to me, but I enjoyed it quite a bit. Not all of it, but much of it.
My interest in Star Wars the brand (not the original movies or those characters) diminished greatly since the Special Editions. From that point on, just about every film iteration, for various reasons, has seemed, to me, like a betrayal of what came before.
I’ve enjoyed some of the supplemental content over the past decade or two, like the better seasons of Clone Wars, a handful of episodes of Rebels, some of the games, some of the comics. But I’ve been burned too many times with the films. I’ll rewatch the Despecialized originals a million times, and they still maintain their magic for me, but Disney/Lucasfilm is going to have to do some serious soul-searching and make significant changes if they want my money in the future.