Secrets of the Wing Commander Universe is a cool book. I'm not really sure why it exists - it was published by a 'serious' computer book publisher and it was done when some of the games covered were years old. Its unofficial-but-popular status also created a bunch of minor non-tinuity errors that took a few years to squash... things like Captain Andropolos' gender. I'm also surprised by how little we hear about it - I worry sometimes that I was too harsh in pointing out how its timeline was 'non canon' back in the late 1990s. You also never see it referenced by Origin folks - you'd think anyone as dedicated as Mark Minasi should have gotten a sly tuckerization or two (Where is he today? Or the person who did that beautiful art of the ships?).
It's a very well done book, though, and everyone should pick it up if they can find it... it gives you a great idea about what the Wing Commander community was like back in those Compuserv days (I wonder if I have any of the old 'Privateer Pilots Guild' newsletters on a disk somewhere...) It's also the book that introduced me Larry Niven by reccomending the 'Man Kzin' series as being Wing-like... it truly isn't, but going through and beyond Niven's canon pretty much defined the kind of sci fi fan I am today. Minasi also reccomended CJ Cherryh, who I didn't like at all. Also, I don't think the book ever mentioned 'Freedom Flight', which would have been around at the time... which is kind of odd.
Allright, as for official guides... I generally define their importance by how much they add to the universe rather than their advice on playing the game (I know, this is the opposite reason from why I just reccomended Secrets of... but I digress). I know how to play Wing Commander, I want tiny facts! TINY FACTS!
The Wing Commander I & II Ultimate Strategy Guide is probably the most 'important'. The oddities of Carl LaFong and his stories aside, that book had a bigger impact on future Wing Commander continuity than pretty much anything... the background it directly established lead to a whole bunch of things, including the Wing Commander Academy TV show, the characterization of Maniac in the later games, various elements of the CCG, bits of Star*Soldier and beyond. I defy you to find a single Wing Commander product that *doesn't* somehow reference or evolve from the WCI&IIUSG. Also, the importance of its 'making of' half can't be undstated - it's a huge part of why many of us fell in love with 'Origin culture' all those years ago.
The two Playtesters Guides add almost nothing to the continuity. They provide some information that's fantastic for 'quick reference' (the sector maps for Armada, the percentages of enemy encounters in Privateer), but nothing we didn't ultimately learn from the games themselves. Their best point was the 'Q&A bios' at the end. Other kids had baseball cards, I had the Playtesters Guide bios! I've met more than one of the people who were my playtesting heroes as a boy since and they've always been horrified and honored that I know who they are already.
(My strangest, strongest story about the playtesters' guides have nothing to do with the books themselves. It was maybe early 1995 and I was sitting on a futon leafing through the Armada guide - learning the sectors, the mission briefings I hadn't unlocked yet, staring at the transports that I hadn't seen yet, etc. It was dark out and my mom noticed this terrified mewing from outside, like one of our cats was dying. We all rushed outside... and it turned out that Sam, our big tomcat, had fallen into the closed pool. He'd somehow slipped through a tear in the pool cover and was drowning. We were incredibly lucky we heard him, we cut through the cover and jumped into this disgusting mess of green goo to try and rescue him. We brought our poor half-drowned cat inside, put him on a towel on the same fouton where I'd been reading... and he immediately peed all over my Armada guide. I was too happy to have recused him to be angry about it at the time... and I still have a cat-peed-on Armada guide in a bag in my closet.)
The Official Guides to Wing Commander III and IV were kind of weak for my purposes. They have tiny, tiny bits of information that you have to strain out (ie, calling the Ajax a 'heavy cruiser' at one point -- that obscure)... but they didn't add anything cool to the continuity. Most of the interesting bits (the newsbrief texts, the Behind the Screens CD) were available through other methods... though I was incredibly impressed when I first saw them in the WC3 book (I'd preordered WC3 at a place that promised a poster and a Behind the Screens CD... I got the poster.) The stuff Chris liked about the WCIV book (the ships, the color section), I'd seen before - at the website and in the WCIII Authorized Guide respectively. The fact that it 'spoiled' the Tolwyn plot when you went to learn about the Arrow was horrifying at the time and is funny in retrospect.
The Authorized Combat Guide to Wing Commander III has a special place in my heart... it doesn't add much, but it tries a lot with the advice sections from the experienced Colonel. I remember being incredibly excited when I first found it in a store - it was months and months after the game was released and it included all sorts of hints about the 3DO version that I hadn't played yet. It also 'invented' the color 'plot' section found in the Wing Commander IV guide. I was never sure exactly *why* they made the book, but it was neat.
The Privateer II book was incredibly expansive (all the mission text, all the layouts, etc. for hundreds of missions), but it didn't add *much* to the continuity beyond a few references in the ships guide. It also explained everything in the story better than the game itself did, which was neat. The best thing about the guide was that it was published over a month before the game came out (since it had a last minute delay in the US). I bought it and swore I wouldn't read it until the game was released... that lasted half of the ride home from the mall.
The Wing Commander Prophecy guide is a cut above the WCIII/IV guides in terms of continuity... although I had a few personal issues with some of the details. It's the source of the 'infamous' 9-trillion-casualties number and a bunch of the bios are kind of awkward... especially the redshirts. It didn't pay enough attention to some parts of the game itself - like Dallas' *name*.
Then the Handbook... I actually consider this to be more of a manual than an official guide, but I can talk about it for days. It adds an amazing amount of detail to the WC universe, it's one of the reasons we have to insist that the movie material is 'canon'... but it also made a lot of bad assumptions as to what the fanbase did and didn't want to hear about. Reworking the start-of-the-war stuff was pointless - and it wasn't a mistake, since the guy who did that book was the same man who did most of the others discussed above. A heck of a guy, but his reasoning for rebooting parts of the story in the Handbook were flawed (especially when none of the other movie material conformed to these changes). My best story about the Handbook is the night I got it. I had every bookstore in the Washington DC area promise to call me when it was available... and somehow a local independant bookstore ended up getting it (ultimately weeks) before anyone else. They called me up at 6 in the evening or so and I begged and begged my mom to take me downtown to get the book... when I got there, the Secret Service had the area blocked off because President Clinton was in the area for something. I had to wait an hour until I could reach the bookstore... and I never voted Democrat again.
(There's another official guide that isn't on this poll - the Wing Commander III PSX Guide, which was only released in Japan... and it's entirely in Japanese, so I have no idea what it's like. It has pretty color pictures of everything, though! (And a specs page for the Behemoth that's entirely blank.)