Only Two Types of People in the World Share
There are 2 types of people in this world. Those who absolutely have to have a headphone jack and those who don't care.
I'm in the latter group, but I think this is largely because I also own AirPods. I'd be curious to know how much, if any, correlation there is between people who aren't bothered by missing the headphone jack and those who own AirPods.
I personally used Bluetooth headphones most of the time pre-AirPods, but I always found them a little more of a pain than wired headphones which "just worked." Even today I find my Sony WH-1000MX3's to be more of a pain than I'd like when moving between devices, but this isn't a pain I have with AirPods.
Anyway, I think a big hurdle to people being more okay with no headphone jack is to have excellent wireless options which don't make you feel like they have any real downsides. AirPods did this better than anyone in last 2016 and a few options like the Samsung Galaxy Buds and Sony WF-1000XM3 are finally starting to get close in terms of ease-of-use. Hopefully we see more options do great, as well as prices come down to these experiences are more universally accessible.