Maybe selling a $1500 phone isn't a good idea.

What about an $800 phone? That is the price of the base model iPhone. That $1599 is to get a fully optioned out iPhone 14 Pro Max with 1TB of storage. Very few people need that much hardware.

Interestingly, the Samsung S23 Ultra with 1TB of storage is $1619. Just a smidge more expensive. Maybe it's the pen?

Samsung often runs aggressive trade-in programs during their launch window. Later, there are first party and third party discounts and deal, plus carrier bundles too.

There's definitely price creep in the iPhone lineup and I'm sure ASP has increased because of it.

I think this is largely due to the new charging port coming to the 15. I know people who refused to buy the 14 because they don't want to be stuck with the lightning port for another 1-2 years.

I doubt most buyers of iPhone care about what port they use. It’s more likely due to really not much exciting things happening in recent updates