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Macworld 2009: My iPhone dilemma

In about 10 minutes, Apple will keynote its last Macworld trade show. For a variety of reasons—Steve Jobs’ inadequately explained new illness, the lack of Jobs at the show, the fact that Apple is leaving after this year—this Macworld is less interesting than most. But I’m still going to be hanging on Phil Schiller’s every word. Because I do have some things I’m curious about. And one of them affects a device I use every day: The iPhone.

Listeners of the Windows Weekly podcast know that I’m interesting in pursuing what I jokingly called “La Vida Microsoft.” This is the SuperSite for Windows, after all, and it seems like I should be focusing first and foremost of Microsoft technologies, especially those that directly impact Windows users. On that note, I’ve been using the Zune exclusively instead of the iPod, for example. (And loving it.) But I’ve been unable to get away from the iPhone. Despite it’s remaining flaws, and there are many (though Apple has dramatically improved the device over the past 18 months), the iPhone is simply the best smart phone there is, and by a wide margin.

That said, data syncing is still a huge problem on the iPhone, for Windows users, a situation where I still feel that I’m the only person out there even communicating this problem. Ideally, I’d be able to sync my Windows Live contacts and calendar directly (i.e. over the air) to the iPhone, but that’s impossible from what I can tell. Not as good, but acceptable, I’d be able to indirectly sync this information to the phone through Outlook on a PC. That, at best, is difficult, and for a variety of reasons.

So. What I’m doing right now is synching contacts via Apple’s lackluster (but, again, getting better) MobileMe service and syncing my Google Calendar via the excellent NuevaSync service. I would be synching Google Gmail Contacts via NuevaSync but I’ve run into a bug getting the master contacts list imported. (This bug doesn’t affect my secondary Google account, so I suspect it will be rectified over time.) Syncing things through Google OTA to the iPhone is good but not great, and getting off of MobileMe is also desirable. Coincidentally, my MobileMe account runs out this week, so depending on the announcements I hear at Macworld, I may finally get rid of it.

Anyway. I’m curious to see if there are any MobileMe/iPhone/Apple online services announcements today. Secondarily, I’d like to figure out a way to get Windows Live data synced to the iPhone. I don’t expect any news in that regard today.

I’m curious if Apple is serious about putting iLife on the Web for everyone to use and what effect, if any, this will have on Microsoft digital media offerings (Windows Live Movie Maker, etc.).

I’m curious is Apple is really entering the home server market, following Microsoft yet again. I doubt they will do this as it doesn’t seem like a good idea, and Apple TV (which is excellent now) hasn’t really set the world on fire, so why bother?

I’m only a little bit interested in a new Mac Mini and only then if it’s truly competitive from a price standpoint. I don’t expect much there.

I’m even less interested in a 17-inch Macbook Pro with a non-removable battery and Apple’s typically over-inflated battery life claims, but that seems to be on the docket as well.

I do expect Apple to announce stellar holiday sales and brag about typically dubious market share claims. I expect the bogus “world’s greenest laptop” claims to continue too.

Well. I guess we’ll see what happens. These are my thoughts and questions about the show before it happens. I won’t be able to do something similar for CES, and Steve Ballmer’s keynote tomorrow, because I’ve already been briefed on that. But it will be interesting to compare the two keynotes, since (among other things) both are lacking their long-term presenters for the first time.

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