> Apple has a really good track record of dropping things at the right time: floppy, CD-ROM, Flash, etc.
Counterexamples to your claim: Thunderbolt? Magsafe? Magsafe2? The physical escape key?
All of your examples were actually significant improvements: floppy / CD-ROM took up immense physical space and removing them caused a significant improvement in space and weight. SSDs initially had less capacity, but at least they had way better performance and also improved upon space and weight.
> The headphone jack is a legacy, bulky port
The headphone jack doesn't save on weight, its alternatives aren't an improvement. It does save on space, and I understand that space is tight on a phone, but honestly, we've already had so many brilliant and slim phones that have headphone jacks that I don't really buy this as an excuse. Do we /really/ need ever so slightly slimmer phones every year? Remember the bent iphone 6es?
I'd be willing to buy this if there was something amazingly novel that USB-C provides for headphones, or if wireless earbuds lasted more than 5-6 hours.
Here's what it comes down to: my 2013 macbook pro is fantastic, and none of the new stuff regarding ports is a genuine improvement to my experience, but all of it adds to potential frustration when I eventually have to make the switch when the hardware can't keep up anymore. I feel similarly with my iphone SE.
I really wish they'd stop futzing around with everything just for trivial improvements.