The prices are what they are. Yeah, it's insane how much phones cost these days but even Android flagships push close to the $1k barrier so I'm not going to get too upset over $100-200 dollars more spread over 15-24 months (my personal upgrade cycle). Plus as a former Android user for 5+ years who recently switched back to an iPhone last year, I just find I enjoy iOS more, and there was always some glaring problem with my old LGs and Samsungs after 6 months to a year, so I'll pay a premium for an iPhone. And I'm not even locked into the Apple ecosystem, it's literally my only Apple product, although I'm admittedly really interested in the new Apple Watch (which will be really interesting to compare to my Garmin Forerunner 235 for fitness tracking since it has a lot more functionality), iPad Pros and AirPods.
The headphone thing is just something pretty much everyone will have to get over eventually, IMO. I'm pretty sure phones with a headphone jack will be a niche product in 5-10 years once bluetooth headphones achieve the right quality/price balance. At least for the average consumer.
The Xr model definitely seems to be pretty overpriced for what it is, hard to argue that for me personally. I also hate the standard storage sizes offered for the money, but again it's just something I'll have to budget for by either paying more sooner or holding onto my current phone longer.