I haven't bought a new iPhone since the 5. I typically would wait a year and buy a used year-old model for half price (with AppleCare). But I didn't do this after the XS, and now with Pro and non-Pro models it's incredibly complex to find the best value since used prices are so dynamic and there are so many models to choose from.

Might be time to just buy a new one with USB-C and use it for 5+ years.