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I bought one of these recently, although it's a fair bit under your budget.
https://www.sony.co.uk/electronics/walkman/nw-a40-series
BT is handy. A 256Gb card for music. Supports hi-def.
With £500, this site is maybe a good place to start - just in case you're not already aware of it ...
Worth a look & to read some reviews. It might throw up a few brands/models you haven’t already heard of.
https://www.advancedmp3players.co.uk/shop/MP3_Players.1/FiiO.406/FIIOX5III/FiiO_X5_3rd_Gen__X5iii__Hi-Res_Player_-_Black.15039.html
The DAC in it is better than my REGA CD player.
Hmmm., another good one to consider - thanks!
how do I get lossless files anyhow ?
https://www.studiowear.co.uk/ -
https://twitter.com/spark240
Facebook - m.me/studiowear.co.uk
Reddit r/newmusicreview
Another good feature, which probably applies to most high end players, is that you can connect USB and it will stream audio out via it's in built DAC. So you can hook it up to your hi-fi if you want, and get the benefit of the DAC.
My portable setup is a little Flac capable SanDisk Clip MP3 player, with some (£300) Westone triple-driver IEM's. I decided to spend my money on the front end and it does the job well enough, but I am reading this thread with interest!
Ok it should just be a case of drag and drop then thanks.