The bulk of this post is my reply to Josh Lowensohn’s post on CNet regarding this week’s Apple WorldWide Developers Conference.  Seemed pretty weak to me, so I essentially wrote my own version.  Go read Josh’s and then read on below and tell me who’s you think is better!

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Really, Josh?  This is all you could come up with for FIVE big questions going into the WWDC?  Aren’t questions #1 and #2 really just parts 1 and 2 of the SAME question: What is the iCloud and how will it work?  Question #3 is valid enough, but again, question #4 should be covered in the detail for the previous questions.  And you’re wondering how low the price will be for Lion?  How about what will be in it that will make it a worthwhile upgrade?  Snow Leopard didn’t cost much, but it didn’t do much either and some incompatibilities made it a problematic upgrade.  Try my five on for size:

1: What is the iCloud and how will it work?  We’ve got lotsa rumors, but no actual details about what will stream, how well it will work, will it work for all platforms currently supported by iTunes, and most importantly, what will it cost.

2: Will there be new hardware?  As I said, a perfectly valid question, but here’s where you should ask about what’s coming AND when will it arrive.  And perhaps, can Apple really get away with releasing what the rumor mill would have us believe will be an incremental upgrade of the iPhone 4 three months out of the by-now usual cycle?  Also, is potentially moving the iPhone introduction to the time of the usual iPod presser a tacit admission that the iPod is pretty much over?

3: Will iOS 5 be good enough to keep iPhone users at home?  THIS is a big question for me, ’cause if they don’t deliver the next-gen iPhone in the June/July timeframe and instead delay it till September, I and many other 3GS owners have a big set of decisions to make.  Do we re-up with the phone we have and hope AT&T will be merciful and let us upgrade in 3 months with only a nominal charge?  Do we blow 2 or 3 bills on the iPhone 4, betting the next version will be underwhelming?  Do we get a burner and swap the SIM to keep our phone service while we wait?  And if so, does that kill our “unlimited” data service that would otherwise be grandfathered in?  [Probably.]  Or do we just bite the bullet, flip Chairman Jobs the bird and get an Android phone, where we don’t have to put up with all this malarky?  If no 5th gen iPhone is in the immediate future, then a deciding factor on what I and others do will be what iOS 5 will do. Will it be a slight upgrade or the kick in the pants that it needs?

4: Will Lion be a substantial, compelling upgrade, or will it be a streamlining/feature fix like Snow Leopard?  Not a big question to me, personally, as a happy Win 7 user, but given that Snow Leopard seemed more like a release for the sake of a release, will Lion (as with iOS 5) be a big ol’ kick up or will it be more of the same but at such a low price no one will make much of a fuss about buying it?

5: Will there be “one last thing?”  Something missing from recent keynotes is a blow-the-doors-off item that Jobs casually throws in just when you think he’s done.  Save for particular details about a given featured product, we’ve pretty much known in advance what Jobs will be talking about at his keynotes for the last three years or so.  Will this change this time?  Could it be a “surprise” introduction of the 5th gen iPhone that blows the rumors out of the water?  It would be wonderful to have all the traditional hyped-up anticipation that precedes these keynotes not get knocked flat by the actual presentation.

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