Or instead I can not spend all that time and effort messing with my phone that holds all of my data and instead but a moondrop phone and never show Samsung my wallet again.
You're actually buying that Moondrop device? Let me know how it goes, seemed like a cool concept but I can't trust them enough to get a mobile device done right
The only headphone jacks worthy of good IEMs are Sony, old LGs and maybe DAPs. That Moondrop device might be an exception but I'd skip a dedicated device and instead buy something I can root and then attach my dongle to, to get around that pesky Android resampling.