Irwin has been using a flip phone for most of his life, but now he is starting to text and texting is a royal hassle on a flip phone. Leo says yes it is! What is the simplest option for him? He doesn't need the latest and greatest. A few apps. Maybe the occasional photo. Leo says that the iPhone is a great first smartphone. Android phones tend to be cheaper, but you want to get a phone that is constantly updated, so you want to be sure your carrier will update regularly. For Android, the Motorola Moto G6 or G7 is a great affordable option. $200-400.
What about buying a used phone? Leo recommends going to Apple and getting a refurbished iPhone. You'll save some money and still have a warranty. Buying refurbs or used from anyone else is just buying someone else's problems. Gazelle, however, is a good third party site that you can trust.