I said that I would wait until the next Big Thing before upgrading everything of mine wholesale to the Apple ecosystem. After asking a lot of people at Best Buy, I've decided that the thing I'll wait for will be the eventual 6G network. So basically, it will probably be around 2030 when I upgrade to Apple.
Also, I discovered that while 2G and 3G are being phased out of service in the next year or two, there are some 4G (and inevitably, 5G) flip phones. That's right, my father can still hold on to his dear Fliposaurus! And then I can wait until the 2030's before I get him a flagship smartphone. I want to put this off for as long as possible because a) nostalgia, I love those dinosaurs, too, and b) I want to contrast between generational technology upgrades to be as dramatic and surreal as possible. Hopefully it doesn't send him into shock.
In the meantime, my next upgrade will probably be the Galaxy Note 10 or 11, which I'll use for educational purposes until it dies on me. After that, I wouldn't mind going for the majority of the 2020's on a flip phone. It wouldn't have as many tools, but its shape and build is ideal to fit in my back pocket when I'm welding. Plus, there's something cool about being the stubborn person from yestergeneration refusing to conform.