iOS has come a long way since those days so a lot of the most common use cases of the past are no longer necessary. But the principle is the same - the hardware is a general-purpose computer but the software is locked down unnecessarily in many ways. Jailbreaking lets you do things that are outside of Apple's box.
The value of general computing freedom is like any other freedom: it is needed when it people are trying to express you.
And not just you. Anyone! So evaluating whether a freedom is necessary turns into a much more nebulous question of “would anyone really need this at one point now or in the future? Is this a thing we should protect in general, even if it does seem like we need it exactly now?”
For example, could Apple/Google at one point be strong armed (by any government) into including spyware onto all devices? And listeners to make sure no one ever says bad things about $DEAR_LEADER?
If the probability of yes is anywhere around 10% over the next decade, maybe it’s a good freedom to have.
Just like most people don’t care about freedom of speech, since they don’t “utilize” it. It’s only utilized when you get sued, and then you can exercise that freedom in court.
IMO we, the techy people, have a responsibility to society to argue for this freedom. Since no one else cares or understands it. But without it it’s too easy for history (in this aspect) to go down a not so good path.
I think, if a deal was struck with Saurik/Cydia Team and Apple to explicitly not do that, there was a much better chance the jailbreaking community would have held.
The downside to jailbreaking was often the instability but that was also back when the phones were way less powerful. Today, armed with LLMs, I would love to have root on my iPhone again. I'd love to rip out Siri and replace it with Claude Code or something like that.
Watusi was great, it let you disable the blue checkmark on Whatsapp. (Since been added as a setting)
I also used a tweak that let me auto-block certain phone prefixes that spammers used. Quite useful.
Was also useful that it allowed you to install multiple copies of an app (such as whatsapp), though no longer a need for that either.
With today’s hardware I might have a different take - the 18 has more than enough hardware to be a laptop so maybe I’d use it for a docking mode. But my gut is I’d probably still want a laptop even then.
To me the upshot is : billions of development, software and hardware, have gone into the platforms - it’s hard to quickly make them significantly better.