AppleIf the time is right for Dad switch to a smartphone from a "dumb" phone, Apple's latest $400 iPhone SE released just this March is the first on the short list.
It's inexpensive, compact, simple to use as it runs the iOS operating system, takes great photos, and it has the potential to last a good, long time since it's running on the same powerful chip as the $700-plus iPhone 11 series. And if anything goes wrong with it, there's a clear and obvious place for him to bring it for repairs or troubleshooting if you're not around — the Apple Store.
The iPhone SE can do almost anything the flagship iPhone 11 series can do. But rather than potentially overwhelming Dad with "all the cool things you can do" with the iPhone SE, your best bet is to focus on a few simpler things that are truly meaningful and improve connecting and communicating, like FaceTime for video calling. Or, if the rest of the family are mostly on Android, Google's Duo video calling app is available in the App Store.
While you're at it, you'd do well to get a nice, simple case to add to the iPhone SE's durability. No need to go crazy here; Apple's own silicone or leather cases are slim and protective.
Honorable Mention: If iPhones are out of the question for whatever reason, I'd recommend Motorola's $250 Moto G Power. It's a larger phone with a larger screen, and it runs on a milder mid-range chip that will still work great for pretty much anything your Dad would want to do on it. The main appeal of the Moto G Power is it's unbeatable battery life. If battery life is a "thing" with your Dad, get this phone. — Antonio Villas-Boas, Senior Tech Reporter