I experienced some calendar downtime for a couple hours on Monday, but otherwise, I’ve not had trouble. Syncing remains almost immediate between the iPhone and the cloud… around every 15 minutes as far as the computer is concerned.

I’m going to have to pay attention to this over the next couple weeks, and I have no intention of shutting down GCal, but I’m surprised how quickly I’ve taken to the calendar function on MobileMe.

So, to answer the question in the title of the post, not yet, but this bears watching.

The App Store will be revolutionary, and I’ve already and installed and started playing with about a dozen of them.

The one thing that does get my heart pumping is the 16GB hard drive. I bought my first phone on 6.29.07 with 4GB, an exercise in planned obsolescence: I figured I’ve save $100 and buy a phone with more capacity in ’08.

But I ran into trouble immediately. I loved the phone so much, used it so much, that 4GB wasn’t enough. I was constantly managing scarcity… juggling small chunks of my music, along with podcasts and audiobooks. I hope that with four times the capacity, I’ll spend one quarter of the time managing it.

We’ll see.

And hey, Chuck gets a (nearly) new phone tomorrow, too. So drinks all around.

FRIDAY UPDATE: A lengthy wait led to a speedy activation (4 minutes, vs. 7 hours for iPhone1 last year) and seamless transition to the new phone.

I’ll be transitioning to iPhone 3G on July 11th, but not without feeling nostalgic for the way Apple’s first iPhone changed how I view phones. (Is that too Apple-centric for your delicate tastes? Well, bite it, won’t you? Perhaps if I had owned a Blackberry, I’d be just as attached to it. But such was not my fortune. I owned a Treo 700p, which was the worst device – I went through two of them trying to get one that went longer than a couple hours without a reboot – I’ve ever purchased. Your mileage may vary; that was my experience.)

But the updated iPhone is almost secondary to the announcement (expected) of Mobile Me and the new commitment to cloud computing unveiled by Apple. I’m excited about the “push” data functionality that will extend to Mail, Contacts and Calendar. But what I’m really interested to see is how this will impact my current array of “software and cloud.”

At present:

Mail: Exchange via Outlook at work; Gmail and .Mac mainly through a browser, secondarily through Mail.app. iPhone accesses Gmail and .Mac mail through IMAP; doesn’t access Exchange.

Calendar: iCal and GCal, synced using Spanning Sync. At work, Google’s sync software keeps Outlook tuned to my GCal. iPhone gets iCal data through a thin white USB cable.

Contacts: Apple Address Book; Gmail contacts are built based on an occasional import of Address Book contacts. This is highly haphazard. Syncing through Spanning Sync’s new contact sync was marginally successful; syncing through Address Book’s new port to Gmail was successful but a big mess. A messy export from Address Book gets my contacts to Outlook. iPhone gets Address Book data through a thin white USB cable.

How will a more complete syncing experience – a more cohesive experience for all my devices, delivered by Mobile Me, assuming Apple actually delivers it – mean for my setup?

One possible scenario:

Mail: beginning next month, iPhone will work with Microsoft Exchange; OS X will extend Exchange to computers when Snow Leopard is released, apparently. That covers work email; my Gmail path may remain unchanged – IMAP; my Mobile Me email will become more compelling with “push” behind it.

Calendar: Mobile Me will maintain one calendar across my computer, iPhone, Windows PC at work and any other device I connect, potentially replacing Spanning Sync, Google’s sync software, and providing a solid challenge to the relevance of GCal in my workflow. iPhone will sync without the thin white USB cable.

Contacts: Mobile Me will easily maintain one set of contacts across all devices, including Outlook at work. And if I can get syncing with Gmail’s contact database to work the way I want it to, it will take care of Gmail, too. Again, for iPhone, no white cable needed.

What I’ve wanted for myself for a long time was the ability to put all of my stuff in the cloud and have access to it seamlessly across all devices. The first piece of that is relatively easy; the second piece has been problematic. Apple seems to be serious about giving users a new experience with the cloud, and I’ll be watching for indications that this is the case.

With those features working flawlessly, plus revamped photo sharing capabilities, document capabilities, and the doubled storage capacity of Mobile Me, it’s possible the successor to .Mac will bring us closer to Merlin Mann’s cherished .Mac dream, and bind those of us who use it more tightly into the Apple orbit, with a suite of tools that will make, to quote Merlin, your entire digital world safe, fun, ubiquitous, and flawlessly integrated.

In my personal scenario, who are the losers if this strategy works? Google Calendar, potentially Google Docs (at least as far as cloud storage of docs is concerned), Spanning Sync, Google Calendar Sync. I’m hesitant to look at my own patterns and divine some greater scenario in which Google suffers because of Mobile Me; for one thing, Google is so big, does it ever suffer? Second, Apple and Google have a great relationship and I would be surprised if their futures weren’t more tightly intertwined around apps like Google Docs, etc.

A few of my favorites:

• The connection with the consumer: “It’s not about pop culture, and it’s not about fooling people, and it’s not about convincing people that they want something they don’t. We figure out what we want. And I think we’re pretty good at having the right discipline to think through whether a lot of other people are going to want it, too. That’s what we get paid to do.”So you can’t go out and ask people, you know, what the next big [thing.] There’s a great quote by Henry Ford, right? He said, ‘If I’d have asked my customers what they wanted, they would have told me “A faster horse.” ‘ “
• On what drives Apple employees: “We don’t get a chance to do that many things, and every one should be really excellent. Because this is our life. Life is brief, and then you die, you know? So this is what we’ve chosen to do with our life. We could be sitting in a monastery somewhere in Japan. We could be out sailing. Some of the [executive team] could be playing golf. They could be running other companies. And we’ve all chosen to do this with our lives. So it better be damn good. It better be worth it. And we think it is.”
• On his demanding reputation: “My job is to not be easy on people. My job is to make them better. My job is to pull things together from different parts of the company and clear the ways and get the resources for the key projects. And to take these great people we have and to push them and make them even better, coming up with more aggressive visions of how it could be.”
• On Apple’s focus: “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully.”
• On his marathon Monday meetings: “When you hire really good people you have to give them a piece of the business and let them run with it. That doesn’t mean I don’t get to kibitz a lot. But the reason you’re hiring them is because you’re going to give them the reins. I want [them] making as good or better decisions than I would. So the way to do that is to have them know everything, not just in their part of the business, but in every part of the business.”So what we do every Monday is we review the whole business. We look at what we sold the week before. We look at every single product under development, products we’re having trouble with, products where the demand is larger than we can make. All the stuff in development, we review. And we do it every single week. I put out an agenda — 80% is the same as it was the last week, and we just walk down it every single week.”We don’t have a lot of process at Apple, but that’s one of the few things we do just to all stay on the same page.”
• And check this out – on catching technology’s next wave: “Things happen fairly slowly, you know. They do. These waves of technology, you can see them way before they happen, and you just have to choose wisely which ones you’re going to surf. If you choose unwisely, then you can waste a lot of energy, but if you choose wisely it actually unfolds fairly slowly. It takes years.”