I was so thrilled when I heard that Snow Leopard (AKA Mac OS X 10.6) would support direct integration with Microsoft Exchange! I even went so far as to force our company (and all seven email users) to suffer a migration from MS Exchange 2003 (which doesn’t work with Snow Leopard) to MS Exchange 2007 (I won’t comment about how thrilled I am to upgrade to software that’s already more than two years old). I am the email administrator and am the decider in these matters!

But now my new setup has been working for about a month and reality is setting in. And that reality is that Apple’s Macintosh equivalents of MS Entourage on the Macintosh and MS Outlook on Windows has its own symptoms of old age and bad design! Now the email rage that was focused on Microsoft is pointed right at Apple!

For instance, you can cannot paste into the location field of an appointment iCal on the Macintosh. That’s right: No cut and paste in that particular field! So if you set up a new appointment and you want to have the location handy on your Blackberry or iPhone, you have to type it in separately, which means you have to remember it or write it down on a piece of paper if you don’t have a screen big enough to see both windows at once.

For instance, Macintosh allows you to add an email address as a new record in Address Book, but you can’t specify which “group” that record will be added to (which controls how the record will be synchronized to other databases). So to make sure that the record is synched to Blackberry, Plaxo, LinkedIn, and other databases. you have to remember to go to Address Book and copy the record into the right group!

I can keep for instancing, but the point is that the level of dysfunction with the Apple software promises to meet and potentially exceed the dysfunction of the Microsoft software! And we’re talking about Apple, the company that can do no wrong…

Recently, I have two experiences that have damaged my ability to do business. The first time, Apple Mail failed to send a file with two attachments that totaled about 18MB. With the help of our email hosting service, Intermedia, we tracked it to a known and discussed issue with Apple Mail’s inability to reliably and quickly deliver emails with attachments larger than about 4MB. That instance might have cost us a relationship with a new investor, because it appeared to them that we couldn’t respond in a timely manner. The second time, Apple Mail sent an email that was truncated because the attachments were placed inline in the text of the message rather than appended at the end of the text. That truncated email got sent to our limited partners and caused tremendous confusion about what we were communicating; made us look foolish with our investors.

I am completely committed to Apple’s platforms since I switched to Macintosh (in 2006) and adopted iPhone in addition to Blackberry (2008). I’m even more committed now that I bought the Snow Leopard story about Exchange integration. But I’m wondering whether Apple really does know software as well as it knows hardware and whether it can fix the issues in its software faster than Microsoft.

I can’t tell you how much it pains me to admit this (given how much fun I have razzing big cell phone operators), but Verizon was right when it constrained the design of the now-venerable Blackberry 8830, the so-called World Edition. the reason I have to confess is that I’ve upgraded to the next one in line, the Blackberry Tour. This is such a compromised device that it proves Verizon’s original premise that wireless is hard enough to do that you have to be careful in adding features to new devices.

I made fun of the 8830 because it didn’t work in the very first country in the world that I took it to (Peru). Along with that, it didn’t have a camera; it didn’t have WiFi; it had a GPS chip that Verizon had disabled. But I’ll tell you this: It did exactly what it was supposed to do reliably and quickly.

My Blackberry Tour, on the other hand, is a total disappointment. The keyboard is smaller than the 8830 so my big fingers constantly hit two keys at once, which never happened before. Worse, the trackball is a new design — rubber instead of plastic, and it has never worked correctly. It appears to have particularly difficulty going left to right (which is really important when you try to correct mistakes made by big fat fingers). The battery life is noticeably shorter than the 8830, so now my phone runs out of juice around 4pm instead of around 8pm on a heavy-usage day. The Tour freezes regularly, either for 10-20 seconds while its processors try to sort out or in a way that requires restarting the device (which doesn’t have a physical on-off button).

The worst thing of all! Sitting right here in my office, where the 8830 worked perfectly, the Tour keeps dropping calls. I’m pretty sure that Verizon’s signal is just as strong and that they haven’t changed towers or antennas, so that means I have an upgraded device that has downgraded radio and isn’t able to maintain calls as well as the earlier device.

So I have an upgraded, much-cooler smartphone that doesn’t work very well. The processor, radio, and battery are all worse than it’s predecessor. I wonder what happened to Verizon along the way that it decided that it was wrong and it should just throw features into the Tour.

Unlike most people, I have two phones, and my other phone is an Apple iPhone 3Gs. I upgraded both phones in the same week four weeks ago. I now find I can type faster on the iPhone, with its improved keyboard software; the iPhone hasn’t crashed or frozen since I bought it; and it has a better browser, better music player, better camera, and much, much better applications platform and environment. Every time the Blackberry asks me for permission yet again to download, install or activate an application or approve its access persmissions, I keep thinking that maybe I should just say no. Installing more stuff on this Blackberry might make it slower or less reliable.

Of course, what happened along the way was the iPhone, which presented a significant competitive threat to Verizon, one that benefited AT&T and changed Verizon’s attitude toward device design. Maybe I should start thinking about porting my primary phone number to the iPhone and abandon the Blackberry entirely. If only AT&T had a network with the performance and reliability of Verizon….

The product has been well reviewed. I just wanted to point out what a great idea it is: Package WiFi and cellular modem in a little device you can carry in your pocket or purse. The product lets you take a WiFi hotspot with you and it works everywhere where’s a cellular signal. My MiFi is on Verizon so it happens to work almost everywhere in the US (except in the lobby of Shutters on the Beach in Santa Monica, CA where I am right now). It worked when I landed this morning and took a taxi to the hotel. It works in my hotel room in Boulder or in Santa Monica (and I don’t have to pay the stupid fee for the hotel WiFi, which often doesn’t work). My particular MiFi came from Verizon, which also supplied my new Blackberry Tour (the upgrade from the 8830), so I got a deal where the MiFi was essentially free (it was an upgrade from my USB cellular modem). So I got a really cool product (well, it does get warm when it’s turned on) for free. Thanks, Novatel!