Mac OS9 Move to OS X: Hardly Trouble-Free, But Worth It, I Think

I have finally moved 90% of my computing life from Macintosh OS 9 (aka Classic Mac) to the gorgeous new OS X to which Apple is fervently hoping most Macintosh users will migrate over the next year or so.

The switch was much more difficult and frustrating than I had anticipated. More than once during the period of adjustment I threatened just to chuck it all and head for Windows XP, a move virtually all of my friends would have applauded if for no other reason than to shut me up about the things Apple did "wrong" in designing and deploying an operating system they don't care about one whit.

Now that I've reached a reasonable accommodation with OS X and am starting to feel reasonably comfortable, I'm glad I made the move. But I have some thoughts about this switch that someone at Apple really needs to hear, I think.

Over the preceding two weeks, I had been struggling with a decison over what OS to switch to from Classic Mac, which I've been using semi-exclusively since the mid-1980's. I have a more than nodding acquaintance with Windows and have spent several months trying to get Linux to work as a desktop environment before giving up that dream.

But I am, at heart, a Mac guy. Ultimately, I couldn't see enough gain from changing hardware, OS, mouse interface, and a bunch of other stuff with no guarantee, of course, that the transition would be any smoother going to Windows.

Most of the Problems are Still Cross-Platform Related

One lesson I learned in all of this was that running OS9 apps in the compatibility box inside OS X is not a great experience. One of the primary reasons I had decided that I had to get out of OS9 was the instability I was experiencing with printing to my Epson SC740 printer. Apps would send files to be printed, then hang without printing. Restart. Files are spooled so they'd print. Or in Word, a document would start to print, Word would crash, the document would print, but the entire system was immediately unstable. Restart.

I finally decided I need a more stable environment. (That was after trying everything I, my friends, and my dealer could come up with to fix the problem including the ubiquitous and inevitable clean system reinstall.)

Meanwhile, I had started work on my first major Open Source project team effort, PythonCard, and the development work there is all being done on Windows. I do have a Win98 box and I also run Virtual PC 3.0 with Win98 in Classic OS. But I was tempted to upgrade my Wintel machine to XP and move there. There were other reasons for considering that move.

After some agonizing and a lot of back-and-forth, I decided that I'd have an ideal setup if I moved to OS X and then upgraded Virtual PC to run XP inside OS X, which rumor has it is quite stable and fast. (Turned out to be an interesting rumor; VPC isn't supporting XP yet. Hmmmmmmm.) That way, I get OS 9, OS X, WinXP (or maybe Win2K) and *nix inside OS X.

Installing OS X is a piece of cake. Went like a charm.

First day or so with the program was trouble-free, but difficult primarily because of the ease of getting lost in the very colorful, rich UI. I'll have more to say about that later in this too-long article.

Then the poop hit the propeller as it were.

First, I noticed that all the printing problems with OS 9 apps not only hadn't gone away or gotten better (no big surprise, really) but had gotten much worse. Applications that formerly printed fine in OS 9 suddenly caused major problems. I made sure I had the latest drivers running under both versions of the OS, but nothing helped.

Finally, I deleted the printer from the OS X Print Center figuring I could just reinstall it and see if that helped. Huge mistake! It took me more than an hour to figure out how to get that deleted printer back. Way too hard.

(By the way, when this was all done, printing remains flaky in OS 9 running inside OS X. Less so if I reboot into OS 9 but not completely healed, either, of course.)

At that point, I was still running Office 98 for Mac. I downloaded an allegedly fully functional OS X version of Office to see if I wanted to move that part of my life to OS X yet. Huge download, at the end of which I find that the stupid morons in Redmond have disabled printing in the trial version. Man, is anyone up there not asleep?

Somehow, networking just stopped working in OS X. I would run Eudora to check mail and get an error accessing the domain. I'd launch IE 5.x and it would not find any servers. OS 9 on the same box was running fine on the Net and as far as I could tell, as was the same. Then I noticed in going through config stuff that IE had a checkbox on "Use Web Proxy for all." I'd never set that and assumed I wouldn't need it since I"m not behind a firewall, so I unchecked it. Bad move as it turns out.

UIltimately, I had to shut down OS X and reboot into OS 9 to get my work done for the evening. I shut down and went to bed disconsolate.

Next morning I woke up, came into my office and restarted my Mac in OS X. Everything worked fine. Yes, Virginia, I did restart the machine several times during the evening when I was working on the problem.

I still have no idea what happened.

But what I began noticing was that moving back and forth between Classic and X is not very seamless at all. For example, if I create a document in an OS X app and I want to open it in OS 9, as far as I could tell, there was just no way to do that. OS X stuff didn't even show up at all in OS 9. Then I discovered that the "users" folder let me get at documents in m personal Documents folder in OS X, but I still can't find a way to get at things, e.g., left on the OS X desktop.

I can't begin to tell you how often I click on the upper right corner of my screen where my trust application menu used to be only to be greeted with the time menu. Yeah, I know. The Dock. Trouble is, it took me several days to get used to this. Apple could have made this easier by the simple expedient of putting a short message at the top of the clock menu, an option I could turn off when I'm comfortable. Something like "It's in the Dock, Stupid!"

At the end of this phase of my experience -- I'm sure much new frustration lies ahead as I delve more deeply in an effort to wean myself completely off OS 9 -- I felt that it would have been somewhat easier to move from OS 9 to WinXP than from OS 9 to OS X. The differences were pretty stark, but the near-similarities were annoying as heck.

For example, from a Save File dialog, there is no obvious way to create a new folder. Turns out there is a small down-pointing triangle next to the "Where" field that brings up a new Finder-like section on the sheet (the new word for dialogs associated with a specific window or its contents) where you can navigate about quite easil and create new folders.

I'll have more to add to this saga over time, I'm sure. But let me close by saying that this whole process would have been orders of magnitude more difficult and annoying if not for the wonderful book, Mac OS X: The Missing Manual by David Pogue. He's one of the best and brighest and most informed of the writers out there doing end-user books. You really need to get your hands on this book if you're going to master -- or even seriously evaluate -- OS X. Kudos to David.