The reasons some Mac lovers stick with OS 9 are practically as numerous as Apple operating systems themselves. There are some OS 9 subscribers who hold out for cost reasons. Computers are prohibitively expensive where they live, and these people would also need to spend thousands on new software licenses and updated hardware (on top of the cost of a new Mac). But many more speak of a genuine preference for OS 9. These users stick around purely because they can and because they think classic Mac OS offers a more pleasant experience than OS X. Creatives in particular speak about some of OS 9’s biggest technical shortcomings in favorable terms. They aren’t in love with the way one app crashing would bring down an entire system, but rather the design elements that can unfortunately lead to that scenario often better suit creative work.
If OS 9 had modern applications and – even moderately – modern hardware, I would be using it. No question. I have an iBook G3 fully working and running OS 9, including important software, within arm’s grasp (I used to have an iMac G3 for the same purpose). It’s difficult to explain, but the reason for me is Platinum, the user interface. OS 9’s Finder, the graphical and behaviourial aspects of the user interface, the speed, the BeOS-like quirkiness – it all adds up to an operating system with a personality that is incredibly pleasant to use, regardless of the hodgepodge house-of-cards internals.
And personality is, unfortunately, what Windows, desktop Linux, macOS, iOS, and Android sorely, sorely lack.
You won’t find personality in any of today’s OSes because they can still be just about anything. The careful branding of Windows 10 and iOS may very well turn into ‘personality’ as soon as they are abandoned.
As for Linux desktops: WindowMaker is so instantly recognisable that it may have personality. I’m not sure it had one when it still had a future, though.
Why would I want my devices to have personality? Devices are there to do what they’re instructed to do. People have personalities.