I love Swift. But I've been adopting it in bits and pieces over the years. It's not just that the language has changed significantly, you also have to get used to the idioms. E.g. my early Swift code often featured Pyramid of Doom patterns, and both language innovations and better familiarity with the idioms have helped a lot with this.
Apple should have never pushed Swift as hard as it did at the time. Between the constant API changes and issues like requiring dynamic framework linkage and copying the whole runtime into every app, it was absolutely not production ready.
We didn't do a simple build scalability test until we were well into the project. If we did it would of revealed swift's build problems to us. Our swift experience is what slowed down our kotlin migration significantly. Today Uber android is still a majority Java app.
Even very recently the experience of working in swift compared to the old obj-c code base isn't as good. To this day there are debugger issues, xcode responsiveness issues and a slower build time.
Hiring on the other hand would be harder now, because it's getting hard to find people who know Objective-C and it's surface ugliness scares new people away. Swift is a decent language if you don't have to have a very large code base, so most people rightfully so don't have that much Objective-C, and if you were to work in Obj-C, you might as well go work at Facebook then.
I havent dabbled in mobile developer platform tooling for the last few years now so I cannot comment on the iOS side, all i remember is that back then it was a shitshow :) Mobile is still playing catch up to how backend infra and tooling operates, I suspect its better but probably still got a long way to go.
The OP indicates that a rewrite was necessary regardless. Even if Swift was not yet mature, do you think it was more worthwhile than rewriting in ObjC? Given that the goal was to "sustain mobile development at Uber for the next 5 years".
Secondly, I'm not a mobile developer so I don't have much context, and I'm wondering about your outlook on iOS development as a whole. Swift obviously had major problems but has supposedly gotten much better. You mention MacStadium's issues, but Apple build servers seem to be making progress with the recent AWS EC2 Mac reveal.
Is the iOS landscape turning a corner, or do you expect a new generation of bad developer experience?