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Again, I would guess that ease of use is in how you use it.

A stock install of OS9 is problematic to a designer because fonts work very differently under OS9 then they do under OS X. That's one of the reasons for the creation of Truetype fonts.

So, now you've got what are called 'the jaggies' in QuarkXPress or InDesign. Meaning, all your fonts are jagged and bitmapped looking. 'cause: stock OS9.

Hey there's an app for that! Adobe makes it. ATM (Adobe Type Manager). Press the button to smooth fonts. Great!

Now you want to activate fonts outside of the main fonts folder - because keeping them in the main fonts folder means they are active and each active font eats a small amount of ram. Like most designers you have thousands of fonts. Having them all active eats lots of ram for no benefit because you don't use all those fonts at once. This is impractical. Well, Adobe makes ATM Deluxe. Great, you can now tell ATM Deluxe which fonts to activate and where they are.

But, oh, guess what? ATM Deluxe doesn't do automatic font activation. Even worse, the next time you activate a font of the same name as a previous one, guess what it does? It activates the previous one, not the one you told it to activate. Now you have problems.

Enter Suitcase, which changed everything in font management. You don't need ATM Deluxe anymore. Yaay! Oh wait! Suitcase is great, but you know what? You still need ATM to smooth fonts because Suitcase doesn't do that.

Welcome to OS9 font management - where OS9 is NOT easy to use!

PS. I abhore ATM Deluxe. There was a time where we sent our files to the printer and we had no end of font problems from that printer. It's because they used ATM Deluxe to activate fonts and EVERY time they activated the fonts WE sent him, ATM activated previously activated fonts in their system and not OURS. Biggest piece of garbage software I've ever had the displeasure to use.
Ohhh, yes. Font management. I forgot about that. o_O
 
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Font management sounds like a real nightmare! They would have definitely had to have fixed that to get Classic OS competitive. Windows 2000 is widely regarded as one of the best Windows releases of all time, what did it have over OS 9 at the time?
 
Windows 2000 is widely regarded as one of the best Windows releases of all time, what did it have over OS 9 at the time?

Off the top of my head:

1. A stable foundation (NT).
2. Preemptive multitasking.
3. True multi-user capabilities with file-/folder-based permissions.
4. A command line.
5. Support for multiple CPUs (up to 32 in Datacenter Server).
6. Support for more than 1.5 GB RAM (up to 64 GB in Datacenter Server).
7. Software RAID (0, 1, 5).
8. Support for more than one architecture during the beta phase (DEC Alpha and x86).
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It would be fun to have a version of Mac OS that uses mach_kernel but has the light interface of the Classic Mac OS. Sort of like Rhapsody or similar but updated.

Coming back to that, I always wondered why Apple didn't provide any default GUI with the Darwin x86 or ppc releases. Sure, you could get XFree86 or Xorg running and then use any X11 window manager or desktop environment you could get to compile - OpenDarwin used GNOME, PureDarwin had an Xfce port IIRC - but... IMHO, it would have been cool if Apple had provided the Rhapsody/DP2 GUI, so that Darwin would sort of have been an entirely unsupported continuation of that line. Since OS X proper had Aqua instead (and all Aqua applications presumably required frameworks that Darwin-plus-Platinum would have lacked, and there'd have been no commercial apps for the x86 release anyway) there'd still have been a very strong incentive to get (a "real" Mac and) full-blown Mac OS X.

Along the same train of thought, I wonder to what extent components like the kernel, device drivers, etc. of the Darwin/x86 releases can be used to modernise a Rhapsody DR2 installation.
 
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Along the same train of thought, I wonder to what extent components like the kernel, device drivers, etc. of the Darwin/x86 releases can be used to modernise a Rhapsody DR2 installation.
I'd imagine quite a bit, assuming everything is coded in the same language and for the same architecture. You'd just have to make sure there were libraries/APIs available for the ported parts of Darwin on DR2.
 
Font management sounds like a real nightmare! They would have definitely had to have fixed that to get Classic OS competitive.
Apple was already moving towards that, but with OS X. In every stock install of OS X ia an app called Font Book. It was Apple's attempt at providing a font manager for pros. Unfortunately, the mechanism they chose for activating fonts was not the best - but Font Book has improved over the years.

Of course there werre underlying system changes that eliminated other problems, such as jagged fonts. You can also still use display and print font sets in OS X (one set was for onscreen display of the font and the other was for printing) but truetype made it so you didn't have to. And OS X was more fully integrated to use TTF.

I'm not so sure any of those modification would have resulted in an OS9.3 - but more of an OS10. However, up until 10.1.5 most designers found OS X backwards and useless for their work so there is that.
 
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I like the idea, but OS 9 actually does have multitasking already. It's just not preemptive multitasking like you're used to. It uses what is called cooperative multitasking. I like that about Mac OS 9. It encourages you to focus more on one thing due to how cooperative multitasking operates.
Especially if that one thing is a disk/system related utility operation. That is to make the priority stack favor the OS over other operations until you are done doing that one thing. It is rare for a modern system to become unstable during a disk utility operation, but it can happen and people don't always stop and wait.

One place you could see that in OS ten was in the days of Boot Camp on Intel Macs. That operation of resizing the host OS while it is booted is an example where the OS operation should be the only thing allowed to happen until it is done; lest you lose the ability to boot your computer.
 
I think the graphic design world would probably disagree with you here. The ability to do other things while you have something else going on in the background means you can be more productive.

Adobe is explicitly aware of this, which is why you can send print jobs or PDF jobs out and continue working. Otherwise, you'd have to wait. A problem if a customer is waiting for that proof or the printer is expecting the PDF.

Of course, everyone's uses for the OS are different but I'm just making a counter argument.
You can do multiple things at the same time. You can run multiple programs at the same time. But you can't run a system level operation or disk utility operation at the same time other actions were taking place. This made it much harder for a system process to crash; ie: installations required that nothing else run in the background. Frankly, I'd prefer to have some things require that the system pause completely. I work in IT and there are people that feel so strongly that they will lose productivity that they will try to run complex and resource intensive software at the same time they are running utilities that make changes to drives, run large installations, etc.

But those same people also are the ones that tie up your time when you remote into assist them with an issue and they haven't restarted their PC in 117 days, but I digress...

The issue is that cooperative multitasking reserves RAM until it is used up and relies on the running application to reliably release it back to the OS when it is done. Most of the crashes that occurred in classic OS (outside of extension/hardware related issues) were almost always because a program wouldn't close properly and RAM would be improperly returned to the OS for use with another process. But you could run iTunes to listen to your streaming radio service, Adobe CS Suite, and your web browser all at the same time. I do it frequently on OS 9 on my PowerBook and iBooks.
 
Mac OS X DP2 did just that!

Thinking about how Mac OS 9 could have grown into a more solid contender...

1. A command line interface.
AppleScript is cool, but doing something simple like a `cat *.txt > combined.txt` was just not easy in the old OS. I know A/UX existed, but I was never able to make it useful for me.

2. Improved Network File sharing
File sharing was slow and unstable at the best of times. I remember setting up a local Hotline server on my home network just for the sake of faster file transfers because connecting over AppleTalk / File Sharing was just downright slow and would bug out if you tried doing anything else. At least with Hotline, I could keep on working while larger transfers processed in the background and it was simple to resume if a transfer failed.

3. Better App Switching
I always had my application menu torn off into the little floating window, but that was a bit of a weak solution compared to something like the OS X dock or a Windows taskbar.

4. A Task Manager
Process overview / CPU usage and background tasks. Hardware monitoring in general would have been nice. But that went against the philosophy of the Mac - the user shouldn't need to consider the hardware, which should just get out of the way and allow you to work productively.

This all comes from years of OS X and Linux use, so if I hadn't have gone down that path, I probably wouldn't really need or want these things.

Some aspects of OS 9 were really great though. The economic use of screen real estate (even more so with System 7) allowed smaller screens (even 640x480 res) to display quite a decent amount of information. Widgets were tight and every pixel counted.

I loved the classic Finder and it's one-to-one "Spatial" approach where a file was a file and a folder could only ever be represented by one window. Anyone interested in the classic spatial UI/UX, I would recommend you read this wonderful Ars Technica article by John Siracusa (2003).

The Finder was a great place for customization, allowing an average user to go deep into the rabbit's hole with custom icons and file / window positioning, which was all stored in that invisible and rather fragile Resource fork.

I always like the idea of the tabbed windows and would be happy to see this feature return to macOS at some stage.

:apple:

(@TSE great thread topic!)
Regarding a couple of these items it was a matter of the time.

4. Windows 3.x didn't really have much in the way of resource monitoring either. That is just the way older computers use to be. If you spent $5,000USD on a computer you didn't want to find out that you couldn't install the basic software and run it. Software use to be built with native code and the foot print was MBs and the RAM requirements were really much smaller. If you aren't trying to shoehorn websites into React wrappers then you can make software that is really much more performant, but it's a sign of the times. You need resource monitoring today.
But Finder did have RAM usage monitoring in the Apple menu about Finder or About Mac (can't remember) it will show you finder, open programs and the RAM usage for each and how much is left to the OS. RAM was really the vital resource. Disk space you managed before you installed an application.

3. The app switching was handled by Switcher in the top right corner of the menu items. The icon showing is the application in focus. If you click then the drop down menu lets you see which applications you can switch to. Since you had only so many applications you can run under 1gb of RAM and in cooperative multitasking, you only had so many to switch to/from.

But your point is taken there were things that needed improvement. It really was a matter of an OS that began in the 1980s hanging on into the new millennium. But there are things that I think OS ten lost in its transition as well. The lightweight nature is something I really wish we could have back as a feature of new OS. You can get something close in the Linux world, but in MacOS where I prefer to be and in Windows where I have to be often because of my profession, it seems that the focus is more on features and less on refinement.

In fact, my biggest complaint about MacOS today is the annual release cycle and the fact that each release seems to be just a little more buggy that the version before. I'd really like to see three year cycles where lots of point releases are made in between and the current OS is really ironed out before trying to add more features.
 
Off the top of my head:

1. A stable foundation (NT).
2. Preemptive multitasking.
3. True multi-user capabilities with file-/folder-based permissions.
4. A command line.
5. Support for multiple CPUs (up to 32 in Datacenter Server).
6. Support for more than 1.5 GB RAM (up to 64 GB in Datacenter Server).
7. Software RAID (0, 1, 5).
8. Support for more than one architecture during the beta phase (DEC Alpha and x86).
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Coming back to that, I always wondered why Apple didn't provide any default GUI with the Darwin x86 or ppc releases. Sure, you could get XFree86 or Xorg running and then use any X11 window manager or desktop environment you could get to compile - OpenDarwin used GNOME, PureDarwin had an Xfce port IIRC - but... IMHO, it would have been cool if Apple had provided the Rhapsody/DP2 GUI, so that Darwin would sort of have been an entirely unsupported continuation of that line. Since OS X proper had Aqua instead (and all Aqua applications presumably required frameworks that Darwin-plus-Platinum would have lacked, and there'd have been no commercial apps for the x86 release anyway) there'd still have been a very strong incentive to get (a "real" Mac and) full-blown Mac OS X.

Along the same train of thought, I wonder to what extent components like the kernel, device drivers, etc. of the Darwin/x86 releases can be used to modernise a Rhapsody DR2 installation.
My guess is that internally Apple was already working on OS X by that point. Apple new that their OS was in trouble before MacOS 8 which was the reason for Copland, and there was a massive wish list there and part of the problem was the massive wish list started to create feature creep and eventually it collapsed under its own weight.

The amount of people trying to get onto the Copland team and the number of things that the company wanted to do with it really paralyzed the development of that OS. When Jobs came back, NeXT OS was really the foundation for OS ten and it was really already under way at this point.

TLDR; I would guess that Apple new that MacOS classic was on life support and really didn't want to double work. They made MacOS full C++ and completely PPC architecture and they added the foundations of the emergent web technology of the day, including Airport. It was enough to usher in the new iMac and iBook lines and OS 9 was the classic footprint to bridge the software compatibility gap with the OS X transition.
 
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