I just finished listening to Episode 16.5 (great episode, by the way; really captured the experience of your typical convention). I wanted to share an experience that related to a question you asked in the panel on accessibility.
I was at Chapters a little while ago, checking out the Star Wars section as usual, and saw someone else looking at the books really closely. He picked up Legacy of the Force: Betrayal and gave it a good look. He was about to buy it and I asked "Have you read many of these?" He said no, he never read a Star Wars book. I told him to put it back, that it told stories about Han and Leia's fully grown-up children. He thanked me, and asked for a recommendation. I sold him the Thrawn Trilogy, and boasted I own and read the vast majority of the Star Wars books and comics. We discussed comics for a moment, and I sold him an omnibus (I think Tales of the Jedi Vol. 1).
I didn't get a commission for selling $50 of merchandise
My point is, that indeed there's such a large backstory, and people starting at Legacy of the Force or Fate of the Jedi are missing too much backstory.
I started reading at the NJO, and slowly backfilled the collection (in terms of buying and reading). The NJO always gave good background on events from other books, and then I'd just be sure to read the book they referred to next (e.g. I read the Corellian Trilogy fairly quickly after Agents of Chaos). And now, the only books I haven't read are X-Wing 2-9 and The New Rebellion (the only books I don't own are Specter of the Past and Vision of the Future, but I read library copies).
I'm hoping that the 20th anniversary re-release of Heir to the Empire will re-vitalise interest in the EU. They should make a nice book timeline, arranged by release date (keeping series together), so that new readers will know where to start. So that a poor soul exploring the Star Wars shelf at the bookstore won't accidentally buy Conviction and be completely lost.
Anyways, that's my 2 cents.
"I must not fear. Fear is the mind-killer. Fear is the little-death that brings total obliteration. I will face my fear. I will permit it to pass over me and through me. And when it has gone past I will turn the inner eye to see its path. Where the fear has gone there will be nothing. Only I will remain."
-Bene Gesserit Litany Against Fear