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Now that Leopard is out and about, the most frequently asked question doesn’t concern Time Machine or Spaces or any of the other 300-plus features and enhancements getting touted by Apple. Rather, the most common question about OS X 10.5 is a fairly practical one: Should I upgrade right now.

Take it from me: You should definitely upgrade right away, because of five amazingly cool features. Or not—you could also put off upgrading to Leopard because of five really dubious things about the OS X update.

Yes—I’m about to argue with myself. Or not.

You see, Leopard really is something of a two-faced cat; it has some truly amazing features that make it look like a “must upgrade now” release. There are also, however, some things about it that you might find truly annoying, making you wish you’d never upgraded. In the end, as with most things, the decision will be yours to make. I hope that the following lists of five good and five bad things, along with my general advice at the end, will help you make the proper decision for your own circumstances.

Positive Rob points to these five cool things about OS X 10.5 that will make this a must-have upgrade:

  1. Screen Sharing: For anyone who has ever tried to help a fellow Mac user, screen sharing—especially when used within iChat —will be a huge timesaver. No more descriptive text such as “no, the button you see next to the red dot, below the title bar, just to the left of the word File.” Instead, just share their screen, and you can demonstrate exactly what it is you’re trying to do, and they can watch. During my testing, speed has been good, even when using screen sharing over long distances and not super-fast connections. With iChat running, screen sharing seemed to just work—in the Finder, it wasn’t quite so reliable. I’ve already saved several hours of troubleshooting time with relatives, thanks to screen sharing.

  2. Spotlight: I had some issues with Spotlight in OS X 10.4, so much so that I rarely used it. In OS X 10.5, though, I have no such complaints. You can now find phrases ( “the dog is pink” ), and use boolean operations to focus search results ( “the dog is pink” AND (painted OR dressed) ).

    The other big complaint about Spotlight in OS X 10.4 was the difficulty in doing a standard filename search. That too has been taken care of: there are now at least three super-easy ways to search by filename (via the menu, a button in the finder, or the name: field in the Spotlight search box), and saving and accessing searches is now much easier. It’s a win all around.

  3. Time Machine: Time Machine is OS X 10.5’s new built-in backup technology, designed to make backing up your key files a set-and-forget proposition. Plug in an external hard drive, enable Time Machine, and stop worrying about lost files. Amazingly, Time Machine really does make it just that simple. When it’s time to restore a lost file, a 3-D space interface (which you’ll either love or hate) makes going back in time a simple drag-and-drop operation. Once you’ve used Time Machine for even a short amount of time, you’ll be amazed at how unprotected you feel when using a machine that lacks a regular, automatic, background backup.

  4. AutoFS: A feature I chose with my second overall pick in Macworld’s Leopard features fantasy draft. And yes, it’s not particularly sexy. But if you work with networked machines, you will come to love AutoFS very quickly. This new networking code makes interacting with networked machines a joy. First, you will no longer bring your machine to a grinding halt if you happen to sleep a Mac that’s attached to another via file sharing. Second, it’s really fast. For instance, you can drag a file over an unmounted server, and it will connect in the background (assuming you’ve connected before the info is stored in your keychain) in under a second. You can then continue to drag-navigate the attached drive, and drop the file exactly where you want it to go. Slick.

  5. Finder Improvements: Even though it looks much the same on the surface, the OS X 10.5 Finder has been rewritten, and improvements can be found throughout. Folders with tons of items in them no longer bring the Finder to its knees. The window settings panel has been improved and simplified, even while adding features such as sortable column view windows and adjustable grid spacing. The new sidebar offers more functionality and looks better doing it. Quick Look (which extends beyond the Finder) lets you see what nearly any document is without actually opening it. The new Cover Flow view is an excellent way to browse folders of movies and pictures. The Spotlight interface gives you access to more of Spotlight’s power, and you can use Spotlight searches on networked Macs. A Path Bar shows you just where you are in the file hierarchy—and you can drag-and-drop things onto the Path Bar. Sharing any folder is now nearly as easy as it was in the OS 7 days.

    In short, the Finder, which has long been a source of frustration for OS X users, is no longer the black sheep of the family. It’s a fast, full-featured file manager that won’t get in the way when you’re looking for your files.

Now, here’s why negative Rob thinks you should take a pass on Leopard:

  1. No Classic Support: While Apple is thrilled to list all the things you’ll find in OS X 10.5, it doesn’t make much of an effort to tell you about the things you’ll be giving up. And one of those things is Classic. If you have programs that you must use in Classic, then you’ll want to hold off on upgrading until that’s no longer the case. As an alternative, you could try SheepSaver, an OS 9 emulator. Note that this isn’t the easiest of programs to get running, and it may not run your application—either at all, or with the same level of support you found in Classic.

  2. Application Compatibility: For the most part, application compatibility under OS X 10.5 has been pretty good—nearly everything runs as it did in OS X 10.4. However, if a key program of yours doesn’t work, then that fact won’t make you feel much better. Pay particular attention if you use older versions of programs—there are reports that Adobe Photoshop 7—admittedly, a five-year-old application—won’t run under 10.5.

    The other area that may prove troublesome for you relates to programs that extend other programs— Sogudi and Saft for Safari; Mail Act-On for Mail; and so on. While there is support for such extensions under Leopard, the way it works has changed, and updates will be required. Browse your key programs’ support sites prior to making the upgrade plunge, to make sure you know what’s going to work or not work.

  3. Stacks: Apple touts Stacks as an amazing innovation in user interface…and I might agree, if it had held to what it was once demonstrated capable of doing. Earlier in Leopard’s developments, Stacks was portrayed (on Apple’s site) as the ability to collect any number of items together and view them in a “virtual folder” that you could then pop-up from the dock to browse through. In the final implementation, however, Stacks is nothing more than a new way to view docked folders; you can’t collect random items together. Put a folder in the dock, and it will spring up on a curve (if you have only a few items in it, or have it set to view by date), or show a window with the folder’s contents. Compared to OS X 10.4, this really isn’t progress at all.

    Even worse, though, Tiger’s navigable pop-up folders in the Dock are gone—you can no longer click-and-hold on a docked folder to pop up a navigable menu showing that folders contents, including navigable sub-folders. With nothing gained but some eye candy (oh, you can see big pretty icons), and the loss of existing functionality, this is one feature that really needed some additional development thought.

  4. Interface: Leopard sports a new 3-D dock, complete with reflections and shadows. The menubar is translucent, as are the menus (though with a different degree of translucence). Frontmost applications now have a large shadow. The sidebar has been revised, and its fonts are now fixed in size (ala iTunes, iPhoto). The blue folder icons you’ve known since, well, forever, are gone, replaced by a set of less-vibrant blue/gray replacements. The Apple logo in the Apple menu is now black, not blue. Generic application document icons are gone, replaced by visual representations of the files’ actual content.

    Good? Bad? Well, that’s really in the eye of the beholder, but to me, it’s bad. The translucent menu bar and menus serve absolutely no functional purpose, and for me, do nothing but annoy me. With certain desktop images, various portions of the main menu become quite hard to see. Text-based web pages can make reading certain menus difficult. The blue-gray folders are nearly identical looking; it’s no longer easy to distinguish Movies from Documents or Pictures with a quick glance.

    You may feel differently about the new interface, but I urge you to spend some time with it before you make a purchase decision, mainly because of the upcoming feature.

  5. Limited control: More so than any other OS X release, OS X 10.5 controls the users’ ability to customize their environment. Consider many of the interface elements I’ve listed above. Given that some of these are polarizing features, it would be nice if users had control over them. But they don’t. Don’t like the 3-D dock? Sorry, you’re stuck with it, unless you move your dock to the side, where it morphs into a 2-D dock. (Use this tip to force that look at screen bottom, too.)

    Want larger text in the Finder’s sidebar, because you’ve got a high-dot-pitch screen? Sorry, can’t do that. Do you prefer Tiger’s docked folder behavior over the new Stacks in OS X 10.5? Sorry, not an option. (Hint: if you like the old behavior better, check out DragThing, which lets you easily create hierarchical folders in docks.)

    Want Time Machine backups to run more often or less often than hourly? Nope, not easily possible. Want to view more than the Name, Kind, and Date Modified columns in your Spotlight search results? You got it, not possible. Dislike the spacey 3-D interface on Time Machine, and wish you could have something without a flying star field? Get used to hyperspace, as it’s here to stay. Dislike the blue-gray folder icons? You can change them one at a time, as you could in previous OS X releases. But changing the default folders takes much more work and help from a third party. Mail has a cool new notes feature…but if you create a to-do out of something on that note, that entry is then highlighted in a garish orange color. Hopefully you’re a fan of garish orange, too, because you can’t change it. Want to change the size or typeface of the fonts in iChat’s Buddy List window? You got it—nope.

    I could go on, but you get the idea: When you purchase Leopard, you’re pretty much stuck with the decisions that Apple has made for you. And while this has always been true of Macs and Apple in general—it’s part of what makes the company’s products so good—I think some of these features are “different” enough that giving the user control over them would be a good thing. After all, given that you can’t please everyone all of the time, letting users control their environment to a larger extent should help sell more copies of OS X.

So should you upgrade now? That’s kind of like asking “Which Mac should I buy?” Any answer I give is slanted by my own perspective, and I don’t know the details of your particular situation. But lack of knowledge has never stopped me before, so here you go…

You should buy now if… If you don’t need Classic or any known-broken apps in OS X 10.5, and you want Leopard’s new features, then yes, buy now. Sure, there are some bugs, and I expect we’ll see a 10.5.1 release sooner rather than later. However, I haven’t run into any show-stopper bugs, I’ve yet to see a kernel panic across three machines, and I’ve had only the odd “minor” application crash.

You should wait if… If you require Classic…of course, you’ll pretty much be waiting forever, as 10.5 marks the real end-of-the-line for OS 9 and Classic. At some point, you’re going to have to find replacements for those programs you’re still using if you want to gain some CPU power. If you don’t find any of Leopard’s new features compelling, then also hold off—there’s certainly nothing wrong with Tiger, and the longer you wait, the better the version of Leopard you eventually acquire will be.

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