Switcher's lament: The case against Mac

Think moving from a Windows PC to a Mac is easy? My experience, and my wife's, may encourage you to think differently. Here's the story:

When my latest Thinkpad began to get unreasonably slow, as Windows laptops often do after a year or so of use, I thought it'd be a good time to jump to the Mac platform for a while to see what the fuss was about. My wife's three-year-old laptop was running out of gas as well, so I thought she and I could make the change together. I was looking forward to an interesting period of learning a new platform, and I thought my wife, a heavy e-mail and Internet user but not someone who enjoys tinkering, would appreciate the fit and finish of products in the Apple ecosystem. I didn't think we'd have to give up much.

I bought a matched pair of MacBooks for us, and, over the holidays, we went cold turkey, leaving the Windows machines at home while we traveled to my wife Jennifer's parents for a 10-day-long holiday stay.

Technologically, it was not the happiest of vacations.

Before I get into the things that have been driving us batty, let me just say that the Apple hardware we moved to is gorgeous, and has been reliable. I'm enjoying the stability of OS X and the genius of the multitouch trackpad. And I love that fact that after I put the MacBook to sleep by closing the lid I don't have to worry about it not starting again when I open it.

But when it comes to the different applications my wife and I use, and to moving data from the Windows realm to the Mac, and to accessing hardware we already have, the process of switching continues to be rocky. Not all of the issues we have are with Apple products, and that's rather the point: No platform exists in a vacuum. People use other apps, and have their own training and preexisting hardware. Switching means overcoming a lot of technological inertia.

User interface
The first hurdle a switcher must leap is the shift to the Mac OS X interface. The shortcut keys and UI conventions of Windows don't apply on a Mac. Some of the changes are easy to make, but some are not. Other UI differences touted as superior by Mac nuts I am getting used to but still don't appreciate. The Mac menu bar is always on the top of the screen, not the application window, so you can end up with a menu bar for one program showing while your workspace is from another. The oddity vanishes with a click of a mouse, but it makes no sense to me, UI theory notwithstanding. And so on. Nothing major, and the concepts are not radically different. It's like learning a new dialect of your mother tongue.

E-mail
Both Jennifer and I were using Outlook on our PCs before we moved to the Mac. I connect to CNET's Exchange servers, and my wife uses POP e-mail hosted by her small company. I loaded up Entourage on my Mac so I could continue to use our corporate servers. I found it a pale imitation of Outlook. It doesn't do as much (no color-coding by rule, for example) and the interface is quirky. There's a three-pane view as there in Outlook, but you can't customize it, and it's a big waster of space. I may learn to accept it, but I don't think so. I put Jennifer on Mac Mail and it's working ok for her for new e-mail.

The real problem was importing messages from Outlook into a Mac Mail app. There's no graceful way. Neither Entourage nor Mac Mail read Outlook PST archive files. There is a workaround: Use the PC version of Thunderbird as an intermediary. It reads PSTs and writes MBox files, which Mac Mail imports. (There's also a paid app, Outlook2Mail, but it didn't work for us). Unfortunately, Mail on Jennifer's Mac would crash after I imported the MBox files from Thunderbird. A little Google searching led me to rebuild the Mac Mail index file, which seems to have fixed the problem. But I moved us to Macs to avoid this kind of hackery.

By the way, Apple says that stronger support for Exchange servers in Mac Mail will be coming in the Snow Leopard release of OS X this year. We'll learn more about this at the January 6 MacWorld keynote.

Calendar and mobile devices
Jennifer can't stand Apple's iCal. There's no week view that shows as much information as you can get in Outlook, and she's been getting invitations to meetings sent from Outlook users without critical information in them.

Personally, I find the calendar in Entourage just fine.

But Jennifer is also a BlackBerry user. To date, we have not found a workable way to sync her Mac and her company's group Yahoo event calendar to the handheld. PocketMac, distributed by RIM, simply does not work for her as advertised. A popular workaround that uses Google services as an intermediary won't work for her either. It requires Jennifer to upgrade her company's Yahoo calendar to the new version, but doing so will cause her colleagues' installations of Intellisync to fail, leaving them without Outlook sync for their calendars. For these reasons, she's now using her old laptop alongside her new Mac, and keeping a paper calendar as well. This is clearly not a workable strategy for her and is causing some friction in our marriage as well. Thanks a lot, Mac.

Photos
Compared to Picasa, which Jennifer and I had been using on our Windows machines, the Mac's iPhoto product is frustrating. Its need to create its own copies of images on our hard disks makes no sense to us.The fact that I have to manually import images into its library is a big drag on my work flow. Picasa simply adds new images on your hard disk when you fire up the program. This is not just a hiccup caused by apps being different on one platform than the other. In this case, the primary app to accomplish a task on the new platform is inferior to the old one. I'm waiting for a better solution.

Music
I have not even tried to move my iTunes library from my PC over to the Mac. The instructions scare me. And that's ridiculous. It's the same program on both platforms--the data should be easy to move.

Other nits
It seems that every day one of us will find something on the Mac that doesn't work as it is supposed to. CNET's VPN application, Aventail, for example, won't reconnect to the company private network if the laptop wakes from sleep, until after I reboot my Mac. This is a problem only on some LANs (like the one at my house), though. And Skype auto-starts on a Mac, even if you ask it not to. In order to disable this, I had to do a Google search to find the secret to disabling auto-start in an OS X dialog box. There's no way to correct this behavior in Skype itself.

We found it very difficult to print photos on our HP ink-jet printer. Although the device came with support for OS X, which is nice, in order to print to the photo tray from within iPhoto, we have to go three levels into an obscure and sadistically-designed dialog box. Every time we want to print a photo. On the PC, photos printed on the right paper automatically. And in the new Picasa, forget it, there's just no way to print to the photo tray on my HP.

Also, in our house we have an HP Media Smart Server, a solid backup device. Apple's Time Machine backup app won't currently backup over the network to this or any other non-Apple network storage product. Fortunately, an upcoming update to the HP software will allow most Time Machine functionality to run over the network on the HP. But until it arrives, we're backing up to local USB hard drives.

Things don't "just work" the way the Apple ads say they do.

Web apps--the great equalizer
One thing that makes switching easier today than it's been in the past: Web apps and cross-platform products. If you use Google apps like Gmail or Google Docs, the Mac is great. Using my favorite Twitter apps, Twhirl and Tweetdeck, was a snap, since they are AIR apps, and AIR runs on both Mac and Windows. My favorite note-taking app Evernote is cross-platform, too (Mac / PC / Web), and after I installed, it automatically downloaded all my notes from the cloud. Cool. I also like being able to sync my data files across my Mac and my desktop PC using Microsoft's free Live Sync (Apple's competitor, Mobile Me, costs $99 a year).

On the other hand, Office 2008 for the Mac bears little resemblance to Office 2007 for Windows. I've just gotten used to the new Windows version of Word and Excel. Now I have to learn a new suite for the Mac?

Back to Windows
There is one thing I really do like about my new MacBook: It is a good laptop for running Vista (using Boot Camp), even if it is a bit expensive for that purpose considering its specs. But after two weeks of resisting, I am dropping back to Vista on my MacBook, at least during this critical week, when I will be covering both MacWorld and CES and will have no patience for a computer that gets in my way and apps that don't work the way they should. Vista and XP also run inside Mac OS X using virtualization apps like VMWare Fusion, which I have tried and find amazing--but a bit slow for production work. Upgrading my MacBook's memory may help performance, and I plan on giving that a try.

I still want to give myself more time to get comfortable with the Mac, but I don't know how much longer I'll be able to stand apps that don't work (like Aventail or HP's printer drivers) or an e-mail product that makes me less productive than Outlook. If I was starting from scratch and buying my first computer, or if neither I nor my wife worked for companies with entrenched non-Mac-friendly e-mail systems, I might be singing a different song. But we're not high school students, we're grownups with serious amounts of technological baggage. The Mac has not been treating us well as we've tried to switch.

Editors' note: Some weeks after this article was published, Rafe posted a follow-up account. Catch up on his further adventures at "Together in harmony: Mac and PC."