I have a lightning-analog dongle on my phone headphones, that works fine. I have another analog headphones on my iPod classic for walks. The terrible catastrophe of taking out the headphone jack is nothing. There's no situation where I'd be listening to my phone and want to charge it, if it's on the charger I have a computer with speakers.
iPhones have like 8-20 hours of charge now, depending on what I'm doing. My old iPod is <4 hours, maybe <2, but it's enough for a walk. And if I'm out, where would I be charging it? I don't usually carry a phone charger and wall wart. If I was out for days, I'd use my laptop to charge it, while listening ON THE LAPTOP, which has analog headphone jacks.