2004:  I’d never owned any Apple product.

2005:  I bought my first Apple product, an iPod Classic.

2007:  I bought my first Apple computer, an iMac, through a friend of a friend’s Apple employee discount.

As of today, I’ve already owned and retired:

• That original iMac
• 2 iPod Classics
• An iPod Shuffle
• iPhone 3
• iPhone 3GS
• iPad

• MacBook Pro 13″
• Apple Cinema Display
• Apple Airport Extreme
• Apple Airport Express
• iPhone 4
• iPad 2
• Apple TV
• MacBook Air 13″ for personal use
• MacBook Air 11″ for work
• Apple Thunderbolt Display for work

But I’m not switching quite yet.  Here’s why:

• No simultaneous voice and data — This is a non-starter. I frequently access the Internet while on a call. AT&T allows it, Verizon doesn’t, because of the nature of CDMA.

• Limited international reach — GSM is the global standard, and just a few months ago I was in Korea making calls and going online with my iPhone. With Verizon instead of AT&T, this wouldn’t have been possible — and this is true in many more countries than not.

• Not an early adopter here — I won’t buy the first Verizon iPhone for the same reason I didn’t buy the original iPhone: First generation new products — and granted ostensibly only the CDMA antenna is new — rarely work as predicted.  I’d wait for the kinks to get worked out first.

• No guarantees of network superiority — I love Verizon’s network, especially in the Bay Area, and switched from it to AT&T only when I wanted a more global network for international travel. That said, no one can really predict at this point how the iPhone will perform on Verizon’s network. (Although it’s hard to imagine worse performance than we get with AT&T).

• Switching costs — Not a sole deciding factor, but given the other concerns, no reason to pay early contract termination fees to plunge into another unknown.

Will be very interested to see how Verizon’s network performs!

I’m in NYC.  I bumped into a couple Google folks — Google folks working on the Nexus One launch.  Sincerely, I congratulated them, knowing it was a big day for Google and imagining how much fun it would be to work on such a product/project.

Jokingly, I brandished my iPhone, teasing that I didn’t think I could switch.

Guess what?  They both had iPhones themselves — pulling them from their pockets to show me!

Coincidentally, today my brother just adopted Google Voice, his new “number for life,” although, luddite yet BlackBerry user that he is, I don’t imagine I’ll see him with an Android phone this decade.

But when I switched to the iPhone over the summer, I needed a new set of tools.  In my typical optimizer (read The Paradox of Choice) fashion, I went crazy with research trying to find the perfect application for my imagined needs.  None were perfect, but I settled on OmniFocus, which required a somewhat-tricky iMac-iPhone configuration to get the wireless sync to function.  OmniFocus had a great user interface, and it worked.  I paid the hefty $80 fee for the Mac application and the $20 fee for the iPhone application and the $99 MobileMe subscription fee that enabled sync — and I was mostly happy.  The only problem was:  I didn’t use it.  It lacked a PC or Web-based client, and it was too inconvenient to rely only on the small screen of my iPhone for my to-do list while at work.

So when Remember the Milk released its new iPhone application on the Apple Store (it already had a Web-based version optimized for the iPhone), I decided to reconsider.

Here are the features and functions I now realize I must have:

• GTD-system “projects” and “contexts” support
• Offline iPhone client (for airplanes and other places without Web access)
• Web-based application –> I realized I need a Web-based application more than a desktop client, because there are few circumstances in which I’d be using my PC at work or my Mac at home without Web access, and I could use my iPhone in those situations!
• Wireless syncing across devices and platforms
• iPhone-editable projects, contexts and text entries

Compare, contrast . . . Remember the Milk is the clear winner.  Lamenting my sunk cost in OmniFocus, I’ve ponied up the $25 for Remember the Milk Pro (which enables iPhone-Web sync) and switched, based on this absurd analysis (click to enlarge):

Yes, I’m a complete loon.

In sum:

• EasyTask Manager met most of my functional needs but was simply too hard to use, both the iPhone and the Web-based applications
• Evernote I consider more of a repository for storing information and isn’t suited for the GTD system and far too slow for an everyday to-do list
• Nozbe lacks an offline iPhone client – a deal-breaker for me
• OmniFocus is expensive and lacks a Web-based client
• Things looks great but didn’t have sync functionality when I last checked and has only a Mac client, no Web access

That left Remember the Milk, the award winning Web-based application now with an iPhone application, as the clear winner.  Most importantly, it works for me:  I’ve been using it daily.

For those following my iPhone trials and tribulations, you know that 2.1 broke my Microsoft Exchange integration of calendar and contacts — neither would sync with 2.1, and 2-3 trips to Genius Bars and multiple calls to Apple support didn’t help.  I still plan to describe the workaround I devised (Plaxo as the hub among applications with MobileMe for wireless sync) in a subsequent post.

Well, it seems to be fixed somehow.  The download and installation took about 30 minutes and was straightforward and without complications.  My iPhone and Exchange calendar and contacts are now synced again.  I would love to understand why, but I suppose I’ll be content that it’s working.  Obviously, for an enterprise application, it is inexcusable and completely unacceptable that it wasn’t working for the past several months.

In brief:  I upgraded to iPhone Firmware 2.1, and my Microsoft Exchange integration broke.  I work at eBay, where we use Microsoft Exchange, Outlook and Web mail.  With my BlackBerry Pearl, everything just worked, without a thought.  With iPhone Firmware 2.0, 2.01 and 2.02, I was delighted that everything just worked too — a seamless transition from RIM, right?  Wrong!  With iPhone Firmware 2.1, email stopped arriving completely and all my contacts and calendar events were deleted from my iPhone and no longer syncing.

This was a disaster because of my setup.  I have a PC at work and a Mac at home, but I have (foolishly?) relied for the past 2 companies and 8 years entirely on my work Outlook to manage my calendar and contacts.  In other words, I have no other complete record of calendar events and contact information other than in Outlook.  With the Exchange integration broken, I now had an empty iPhone calendar and empty contacts.  Nothing, no ability even to call anyone without looking up their number in Outlook.  (No one memorizes numbers in this day and age, do they?)

Realizing this is a dangerous dependency, I recently had started to look to backup my data online.  First, I installed Yahoo! Autosync to sync Outlook with Yahoo! Address Book and Yahoo! Calendar.  This didn’t work very well.  I have close to 1000 contacts records in Outlook.  Inevitably, the number of contacts, in Yahoo! Address Book didn’t match the number in Outlook, Yahoo! Autosync failed to merge records for the same person, and, in many cases, critical information was missing.  Probably some sort of problem with field mapping.  Inelegant.

Second, I exported my Outlook contacts to a comma-delimited .csv file and then imported them into Gmail.  This had the same problem as Yahoo! Autosync — mismatched record counts, non-merged records and missing data.  I also tried Google Calendar sync to sync between Outlook and Gcal.  This worked fairly well but takes an inordinately long time to complete; I think the application starts afresh with every sync.

With broken Exchange integration and no clear solutions on Apple’s discussion boards, I now needed an alternative method to get calendar and contacts synced with my iPhone.

Here’s what I want:

• Ubiquitous access to email, contacts and calendar — from my work desktop, from my home desktop, from any Web terminal and from my mobile device . . . . For me, this means Outlook, Web mail, Gmail/Gcal, Yahoo mail/Address Book/Calendar, Mac Address Book/iCal and iPhone
• Uniform data — no duplication of entries, no omitted entries and consistent data across platforms
• Over-the-air sync — what good is a mobile device if I have to plug it in to get data on it?

Clearly, as much as Apple claims to be targeting enterprises with the iPhone, Apple isn’t ready.  They don’t even use Exchange at Apple is my understanding.  They don’t understand enterprise activation.  They don’t understand Enterprise-level support:  After several calls to Apple, their ultimate advice was:  We have no idea why Exchange broke, too bad, good luck.  Thankfully, email spontaneously restored after a couple of days, but I will no longer trust to the Exchange integration for my calendar and contacts, which remained broken last time I attempted to integrate.

Next post, the available options.

Recall my most recent complaints:  (1) abysmal battery life and (2) broken Microsoft Exchange integration.

I was sometimes getting less than 5 hours of battery life, even after Apple replaced my unit with a new one.  Firmware 2.1 plus some more prudent battery conservation practices have all but solved #1.  I’ve read too many articles, blog posts and discussion board threads on this to recount.  Plus, I’ve finally succumbed to logical suggestions — most of which I daresay I had heard already — from BW and ES.  Here’s what’s worked for me:

First, I’m only fetching data now, and only hourly.  Such is the disappointment of and lowered expectations in performance of the iPhone 3G that the very reason for buying it — push — is what must be disabled to provide more reasonable battery life.  I’m not even upset that I don’t get push, because it was working so poorly — that battery-killing wheel seemed to be spinning constantly — and I’m so grateful for longer battery life.

Second, I’ve slightly reduced the number of accounts from which I’m fetching data.  I have work Exchange, Yahoo, Gmail and MobileMe accounts.  Instead of fetching data from all of them, I’m forwarding Gmail to Yahoo and fetching from Yahoo.  I use MobileMe only for calendar and contacts syncing, so I have it set up but never check that email.  And I’m even fetching from my work email account.  I came to terms with the fact that I don’t need push email to distract me in meetings, and I already get push when sitting in front of my destop with Outlook open.

Third, I’ve turned brightness down fairly low.  Even with a protective film on the glass, it’s still bright enough for me.

Fourth, I’ve left Bluetooth and Location Services on.  I use my Bluetooth headset to and from work every day, it’s too much of a pain to go into Settings to deactivate and activate it repeatedly, and I’m not convinced it’s a drain on the battery.  For Location Services, much of the time I have this off, but I just end up switching it on when prompted when using Google Maps or some other geo-aware application that calls for it.

Finally, I’ve left both 3G and Data Roaming turned on.  As eBay alumnus Ryan Spoon notes, push has a much greater effect on battery life than 3G.  I know at least one other iPhone 3G owner — ES –  who switches off 3G not because of the perceived battery life drain but because he believes the network is unreliable and results in dropped calls.  I’m accessing the Internet often enough that I want the speed from its being on all the time.

The net effect?  I can go over a day without recharging.  And I don’t live in constant fear of a sudden drained-battery-induced shutdown.  Frackin’ fantastic.  Reasonable battery life?  Check!

Next, I’ll bemoan the complete failure of Exchange integration, my data sync requirements and then the awkward but functioning solutions I’ve devised.

Today, Apple released the new 2.1 firmware, and it’s broken my Exchange integration.  Right now, I have no calendar, no contacts and no email — the unit is useless to me without these core functions.  I’ve tried deleting the Exchange account and re-adding it, but that doesn’t help.  Apple support forums indicate that at least a few others are experiencing the same problem.  Frankly, I’m sick of the inability of the iPhone to perform basic functions, and I’m seriously thinking about switching back to BlackBerry.

Two reasons to buy Apple products:  (1) They just work and (2) sex appeal.  So far, (1) is absent leaving my iPhone decidely unsexy. 

Must Have:

• Improve the battery life. The battery life is so bad that I find myself now becoming accustomed to charging my iPhone throughout the day. Granted, my usage is high. I ran the unit several times until it shut down to maximize battery life as an Apple Genius recommended. But any handheld communications-organization device needs to be able to run from the time I wake until the time I sleep. End of story.
• To-Do List/Notes Sync. I used Notes and the To-Do List (the “NextAction” add-on) extensively on my BlackBerry, and they integrated beautifully with Outlook, including Outlook Exchange Web mail. Now, I remain in a quandary as to what to do with the iPhone. I’m looking at Evernote, EasyTask Manager and OmniFocus as replacements (I’m a partial GTD adherent), but none solve all of the problems I have. (More on GTD applications to come).
• Copy/Cut-Paste. It’s beyond my understanding why this is not available.
• More Robust Email. The litany of issues is too long to enumerate. BlackBerry is way better, period. This is essential if Apple wants to steal share in the enterprise market.
• Voice Dialing. Especially in California, where headsets are now required by law when driving, easy dialing while in the car is essential. Favorites, Recents, Contacts — all of these are too difficult to use when driving. I’ve tried the SpeechCloud Voice Dialer application and it (1) isn’t a dialer – it’s a voice recognition lookup tool and (2) it doesn’t work well. In 4-5 tries, it never found the name I was seeking, and I then uninstalled it. In general, contact and phone number lookup on the iPhone require too many keystrokes, and the ease of use of the basic phone function is less than ideal.
• Overall Stability. My iPhone crashes. Not infrequently. Usually when flipping among applications. An open platform is great. It’s got to be more stable that this.

Nice to Have:

• IR Beam. Remember the Palm V? I do. I’d love better capability to transmit data from phone-to-phone.
• Video Recording. This isn’t that important to me, but I look forward to the day.

I’m still a satisifed promoter of the iPhone and look forward to future improvements. It’s been a week, and I’m still having fun.