I know lots of people will be really happy with this, but I probably would have traded the jack for water resistance
Honestly, I did try to embrace this trend by buying a Nexus 6P when it came out in 2015. I thought I'll just get used to it. I did not. Besides being a pain in the rear to use with one hand, it ripped holes through my pockets with its sharp corners. So when they then announced the (5") Pixel 1 a year later, I bought one immediately and it's still my primary phone. Still, it's a tad larger than would be comfortable, I find it that iPhone 5 (or 5S or 1st gen SE) is an ideal size for me. The only problem with these is that they run iOS.
Also, even if when new they might be water tight, after you leave it in the sun the glue that holds the phone together and seals it will melt and age. On a samsung I discovered that above the buttons it had less than 1 mm of glue.
1) My car stereo doesn't have Bluetooth.
2) Very few earbuds fit my ears comfortably. After a lot of experimenting I've found a couple wired models that do fit my ears fine. Given the cost and limited selection of wireless earbuds, finding a good pair will be a chore, if I even can.
3) Once in a while having two ports is handy.
There are probably dongle solutions to 1 and 3, and maybe I can find some that fit my ears well. But that all sounds like way more hassle than just not buying phones that have been designed to exclude some pretty basic functionality.
This you can fix easily with a $30 dongle that stays in a car, some of them will power on and start playing from where you left off when power is applied (i.e., when you start the car, provided you leave it plugged in).
I don't use Bluetooth headphones, but for the car, it's perfect.
I also have saved many a social music situation when someone was having bluetooth pairing issues and I just busted out my aux cable, plugged and and blammo the party has music. I'm an IT guy, could I have fixed the bluetooth pairing? Probably. But not quicker than just plugging in.
So we're out there, THERE ARE DOZENS OF US! :)
13 hour flight, airports, etc... fewer dongles, fewer things to charge, etc.
(I have an inexpensive set of cabled noise cancelling earphones that run off a single AAA battery, which always gets packed in my carryon...)
A couple of phones did have a decent dac/amp combo built in (HTC 10, and some LG phones), FWIW.
Since then I have been using the NextDrive SpectraX. I highly recommend it, it sounds even better than the HTC 10, and now I can use (almost) whatever phone I want.
edit: Oops, I missed that you specified you were already using a DragonFly. Is that not as good as the HTC 10 was? I would have thought it'd be better...
I still appreciate a good headphone jack though. The usb-c connectors aren't always reliable and ignoring inline controls. A phone with a solid DAC & amp would be best. Unfortunately it seems only LG make those these days and their Android skin is horrible.
One thing with the 10 was that security updates were basically nonexistent. You got one or two major OS updates, but nothing in between, and nothing after. Lots of phones have this problem, but then again some don't.
Worse than that, the Oreo update completely broke my phone. I went from 2-3 days of battery life with my typical, light usage to something like 12-16 hours with NO usage, screen completely off the entire time. Fixing that required downgrading to Nougat, which required S-OFF, which required me physically mailing my phone to a hacker group and paying around $35. And of course this left me a year or more behind in security patches.
Based on the xda thread about this, it affected lots of people, but was never acknowledged or fixed. Consider yourself lucky :)
The LG phones are, one would hope, not this bad. But still, my takeaway from the experience is that tethering (heh) oneself to a single model or line or phones is really, really bad. The inconvenience of the dongle is, in retrospect, only slightly annoying in comparison.
And there can be significant cost savings. My Moto G6 and SpectraX together cost less than one of LG's phones, and I expect to reuse the SpectraX with my next phone as well. Buying a new DAC/AMP every 1-3 years doesn't really seem right, does it?