>At what point did the old Apple cross the threshold to "modern" Apple?

The simple answer would be when SJ passed away. The long answer is there wasn't a turning point, but a long period of cultural shift, due to Tim Cook being CEO.

Tim Cook not immediately taking a CEO stand and left a power vacuum was a mistake. He said himself he thought everything would continue as normal, which obviously did not happen. Firing Scott Forstall was a mistake. Ive taking over software design was a mistake. Not listening to the advice of Katie Cotton and manage a new PR direction was a mistake. Following Phill Schiller advice of firing long time Marketing Firm for Apple was a mistake. Tim Cook not understanding his weakness which is his judgement of character was a big big mistakes, as it leads to Dixon CEO and Burberry CEO taking helms of Apple Retail, ultimately stoping if not reversed the momentum of Apple Retails improvement and expansion by 10 years. Giving Ive the power to play around with Retail Design because Apple Retail Store is somehow a "social place" was a big mistake. Prioritising Operational and Supply Chain Decisions over Design was a mistake after around iPhone 8 Plus. Too focused on sales metric and bottom line was a big mistake. Shifting to Services Revenue, which should have been AppleCare, iCloud or even iPhone Subscription model, instead they got Apple TV+, in my option is a mistake. They were too scared to hurt the relationship with Carriers. Eddy Cue taking over a lot of decisions? Apple going to Davos? Merging of different iOS and macOS team where it used to be teams per product but later became functions per team structure. Trusting China and didn't diversify their production when Trump was first time in Office. ( They said they will but they didn't. Literally every single media lied on behalf of Apple ). I mean the list goes on and on.

I really like someone on HN said about Apple. Ever since Steve Jobs passed away Apple has been left on auto pilot mode for most of its time.