I was a member since the very beginning, and in the beginning it delivered: some great video content, early looks at trailers/etc., and Photoreceptor (which was the main reason I subscribed - all those amazing cut scene photos, behind the scenes looks, weird Holiday Special shots, etc.). It was great at the start, and worth every cent for me.
But then Photoreceptor stopped. The video content was very sparse, and rarely delivered anything as exciting as the initial hype promised. There were a few other vaguely interesting things, but nothing I should have been paying money for. And the Insider? I totally echo what Erikstormtrooper said about it: for years it's been way too focused on hyping the prequels, in particular the next upcoming film. Content that I used to love (the Wonder Column and David West Reynolds' cut scenes articles were great examples) disappeared in favor of fluff I didn't care about. I used to read every word of the Insider from cover to cover. Now I find myself skimming through, maybe reading the odd article now and again, but mostly finding myself bored because 90% of the content was about the prequels.
Well, now the prequels are over, and there are no upcoming films to hype. The fair weather fans are going to fade away now, leaving the lifetime fans to carry on. It's time to get back to supporting those core fans.
The bottom line is this: there are no more films coming out. Star Wars is no longer the gigantic hype machine it was when new movies were around the corner. There is no reason to expect that people are going to want to pay for content anymore, and Lucasfilm shouldn't be able to get away with charging for it now. It's time for them to go back to all free content again, and for the Insider to get back to the kind of articles that used to make me eager and excited to read each issue.
--SKot