The headphone jack is not a big issue; a good enough USB to 3.5mm DAC is $20 or so.
But. A few years later the usb port is almost unusable.
Also note that, at least for this old phone, Sony updates stopped two years from when the phone was released which is pretty bad, especially as I bought it a year after it was released.
I understand that some people are still upset about headphone jacks. When Apple first pushed that direction, people convinced me to be upset too. But then I broke down, and went on Amazon and realized that quality Bluetooth headphones are plentiful and cheap and only need charging once or twice a month. After trying a pair, I felt silly for waiting so long.
So I'm sure there is SOME audience of people with $500+ Sennheiser headphones, trying to somehow produce an audiophile experience on a cell phone. But the reality is that 99% of normal consumers are better off going wireless and getting the improved water resistance if not better use of space.