I take pills for attention deficit disorder. I lose stuff. I lose corded and cordless headphones multiple times a month. And hey, I know my inattentiveness to be an annoying end of a spectrum. People have things going on in their lives. Not everyone neatly takes care of their in-separate-ears tiny bluetooth speakers. We're a segment of the market.
They're betting that they can do better without the likes of us -- lose some, earn more from the rest. Maybe their cash position enables them to take such risks.
I imagine a headphone jack must use a lot of space within the case, which creates a lot of hardware design headaches that go beyond waterproofing.
I see some people at my workplace who walk around all day with a full bluetooth headset around their neck (not earbuds, like the big cans type) even when not in use, almost as a fashion accessory or statement. Perhaps you could experiment with those kinds of bluetooth headsets if you upgrade to a new iPhone. Obviously that doesn't solve your headset needs for running though, grumble grumble.
I lose stuff too. I just find it eventually.
Granted, it's harder to lose the entire case, though it's still small enough and made of slippery plastic that can slide out of pockets if you're unlucky.
The headphone jack uproar was a tempest in a teapot. Apple saw the stats that either a) people use the headphone that come with the phone or b) they upgrade to wireless headphones. The small group of people using expensive wired headphones can afford an additional $7 permanent attachment.
Yes, Apple prioritizes size and design over everything else. Removable batteries add size, weight, and likely impact the water proof ability of the device. Even when I had a phone that could easily swap batteries I never bought additional ones because they were not cheap and would be discarded when I got a new phone.
I'll also say that I'm happy with the change Apple did here. They failed at communicating it, but I have been on the receiving end of an older phone that would shutdown/crash with plenty of battery left, and would have preferred it to slow down so I could at least use it.