I used to travel with music the way you did. When I bought a Sony WM1Z DAP the sound quality was night and day better, not to mention no need for the laptop, that I have not used my laptop since. I have more music than the storage capabilities of the Sony but that was solved putting the rest of my library on a micro SD card. I also purchased an A&K SP2000 which allows me to stream Tidal and Roon ARC as well. I think you would be best served by a DAP if sound quality is first priority.
I have thought about selling my Sony DAP and related accessories as I don’t need 2 but I like gear. If you are interested in a deal on an amazing Sony DAP.
john