My take on headphones is that noise cancelling is great for long haul flights where there is a constant noise that they can effectively cancel, but more or less ineffective for other, more sporadic noises such as human voices. So I would go for a good pair of IEMs, with tips that give a good seal, which is absolutely vital for both isolation and sound quality.
I spend a lot of time away from home, and I use a Sony NW-ZX2 now superseded by a newer model) to carry my music collection around with me, used with Shure SE846 IEMs. I also have a Dragonfly Red - needs must, as my iPhone has no headphone socket. The Dragonfly is very good, but I definitely prefer the Sony player for sound quality. (There was a comparative review of these two items, which said that the Dragonfly was better - possibly with different headphones - but for me, the Sony wins hands down.) I haven’t heard the new Cobalt, though.
The other issue I have is that connecting any Dragonfly to a phone is cumbersome. It doesn’t sit neatly in your pocket, or even in your hand. It also drains the battery in your phone. So I much prefer to use my Sony portable for music, freeing up my phone for other duties.
In terms of connections, my Sony player has enough local storage for my needs, but also has UPnP built in, so I can use it to play from networ storage if I need to, as well as from web based streams such as Tidal.