Product marketing: they offered dozens of ever-changing models which meant customers didn't have simple purchasing choices, they priced things horribly
Engineering: they couldn't build OS foundations, they bet on the wrong architecture & techs repeatedly which meant they couldn't benefit from rapid drop in costs
Strategy: they had a bunch of half-assed efforts (ahem A-UX) and didn't see where the market was going with hardware and failed to compete against PC clones
R&D: they wound up investing in a ton of pie in the sky stuff that was way too early for market
This type of work, as cool as it was, was them basically coasting off the investment they'd put into UX and computing frontiers in the 80s, like Hypercard which came out in 1987. Nobody else really invested in UX in the 80s so Apple wound up with a decade+ lead, a bunch of great UX talent, and a loyal fan base. But they were basically a UX house atop a zombie corp.
I got my start programming before Hypercard, however Hypercard made it even more fun. It is likely a large reason I am a professional developer today. You could build stuff to do things with minimal to no code and if you add a bit of code? Magic happens. Absolute Magic.
I don't know, maybe it is just me. I've used ASM, C, C++, and a bazillion other languages, yet I always find myself coming back to the simple stuff to get things done.
Déjà Vu, Uninvited, Shadowgate, and Déjà Vu II. [1]
They are all classic point-click adventure games played in first person perspective. Lots of intrigue, some horror (Uninvited and Shadowgate), weird music, good writing. Very fun games!
I believe they can all be played in the browser though a classic Mac emulator on archive.org [2].
Scummvm too, you need to compile it with --enable-all-engines on the configure command.
Comparatively, on PC I never saw CGA graphics which I didn't think were anything but compromised EGA images, which were themselves degraded from VGA images etc. Did anyone else play Prince of Persia on a CGA display?
There was a program called "SimCGA" which would fool programs into thinking you had a color CGA graphics adapter so it would run.
Visually, it was awful. But the novelty of playing games on a battery-powered IBM made up for it.
She also created the playing card art for Windows 3.x solitaire.
Regarding Chicago, I keep seeing its TrueType imitation (which isn't as beautiful as the bitmap version, but is distinctive) everywhere.