I’ve been liking my Astell&Kern SR25 player. Although it is wifi only so I have to make a hotspot for Spotify to work on the road. Flacs sound pretty good on it, far better than any phone. The. UI is very minimal and built around the local music player with other apps hidden away.
I don’t know about one for personalities (I try not to get too invested in an artist’s personal beliefs) but for finding similar artists, I like to use Spotify artist network which maps out similar artists as nodes and lines using Spotify’s api. It’s pretty good for finding artists with similar vibes.