The idea of moving from a Windows PC to an Apple Macintosh may sound appealing. But Rafe Needleman's recent experiences show the switch can be far from straightforward

Think moving from a Windows PC to a Mac is easy? CNET Webware editor Rafe Needleman says his recent experiences may make you reconsider. 

When my latest ThinkPad began to get unreasonably slow, as Windows laptops often do after a year or so of use, I thought it would be a good time to move to the Mac platform for a while to see what all the fuss was about. My wife's three-year-old laptop was also running out of steam, so I thought we could make the change together.

I was looking forward to an interesting period of learning a new platform, and thought my wife, a heavy email 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.

We bought ourselves a matched pair of MacBooks and went cold turkey over the holidays, leaving the Windows machines at home while we travelled to my wife Jennifer's parents for a 10-day stay. Technologically, it was not the happiest of breaks.

Before I get into the things that have been driving us batty, let me just say 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 once I've put the MacBook to sleep by closing the lid, I don't have to worry about it not restarting when I open it.

But when it comes to the applications my wife and I use, and moving data from Windows to Mac, and accessing hardware we already have, the process of switching continues to be rocky. Not all 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 hardware. Switching means overcoming a lot of technological inertia.

User interface
The first hurdle anyone switching from a Windows PC must negotiate is the shift to the Mac OS X interface. The shortcut keys and user interface conventions of Windows don't apply on a Mac. Some of the changes are easy to make, but others are not. I am getting used to other user interface differences touted as superior by Mac nuts, even though I don't appreciate them.

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, user-interface 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.

Email
Both Jennifer and I were using Outlook on our PCs before we moved to the Mac. I connect to work Exchange servers, and my wife uses POP email 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 colour-coding by rule, for example — and the interface is quirky.

There is a three-pane view, as in Outlook, but you can't customise it, and it's a big waste of space. I may learn to accept it, but I don't think so. I put Jennifer on Mac Mail and it's working satisfactorily for her new email.

The real problem was importing messages from Outlook into a Mac Mail app. There's no easy way of doing it. Neither Entourage nor Mac Mail reads Outlook PST archive files. There is a workaround: use the PC version of Mozilla Thunderbird as an intermediary. It reads PSTs and writes MBox files, which Mac Mail imports. There is 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.

Apple says stronger support for Exchange severs in Mac Mail will be coming in the Snow Leopard release of OS X this year.

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 and is causing some friction in our marriage as well. Thanks a lot, Mac.

Photos
Compared with Picasa, which Jennifer and I had been using on our Windows machines, the Mac's iPhoto product is frustrating. Its need to create copies of images on our hard disks makes no sense to us. Having to import...

...images manually into its library is a big drag on my workflow. Picasa simply adds new images on your hard disk when you fire up the program.

The problem with iPhoto is not just a hiccup caused by apps differing between the two platforms. 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 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 gripes
It seems every day one of us finds something on the Mac that doesn't work as it is supposed to. My work VPN application, Aventail, for example, won't reconnect to the company private network if the laptop wakes from sleep, until I reboot my Mac. This problem only occurs on some LANs, such as the one at my house. And Skype auto-starts on a Mac even if you ask it not to. To disable this, I had to do a Google search to find the secret to disabling auto-start in an OS X dialogue box. There's no way to correct this behaviour in Skype itself.

We found it very difficult to print photos on our HP inkjet printer. The device came with support for OS X, but to print to the photo tray from within iPhoto, we have to go three levels into an obscure and sadistically-designed dialogue box every time. On the PC, photos are printed on the right paper automatically.

Also, in our house we have an HP Media Smart Server, a solid backup device. Apple's Time Machine backup app won't back up 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", as the Apple ads say they do.

Web apps — the great equalisers
One thing that makes switching easier today than it has been in the past: web apps and cross-platform products. If you use Google apps such as Gmail or Google Docs, the Mac is great. Using my favourite Twitter apps, Twhirl and Tweetdeck, was easy, since they are AIR apps, and AIR runs on Mac and Windows.

My favourite note-taking app, Evernote, is cross-platform too and, after I installed, it automatically downloaded all my notes from the cloud. 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 got 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 little 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 virtualisation apps such as 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 to try that.

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, such as Aventail or HP's printer drivers, or an email product that makes me less productive than Outlook.

If I were starting from scratch and buying my first computer, or if neither I nor my wife worked for companies with entrenched non-Mac-friendly email systems, I might be singing a different song.

But we're not school kids. We are grownups with serious amounts of technological baggage. The Mac has not been treating us well as we've tried to switch.

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