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If you need flac, absolutely NO radio, and wired headphones... I'd look at old devices that support flashing the Rockbox custom firmware. You can probably find something used with over 128GB storage for under your price point.
Rockbox supports almost any audio type you can imagine (flac, mp3, wma, chiptune formats like spc and nsf, tracker formats like xm and it, anything). It beats out the old click wheel iPod OS in terms of functionality. Playlists, construct a temp playlist while listening to other music, shuffle the playlist, shuffle the queue, shuffle a subsection, play all songs, play albums, play all by an artist, play all in a genre tag, etc. Everything you could expect and probably more.
Ever wanted to play Doom on crappy mp3 player controls? How about a janky proof of concept GameBoy emulator?
Rockbox is deeply customizable, but that also includes themes that mimic the default old school iPod OS or other old MP3 players if you want simplicity. It connects to a computer as a standard flash drive. No software needed for sync, no stupid MTP protocol making file transfers take stupidly long.
I think that it does support a few devices with FM radio, so you'd have to check that. The Sansa Clip Plus suggestion someone else made is one of the supported devices with FM radio. There's an incredibly slight chance it supports some device with Bluetooth, but take a look at the project site and tell me if you really think it does. I'd be shocked.
Also, probably outisde of your price range, but old iPod Classics don't have FM hardware, and up to 6th gen support flashing Rockbox as the OS. Apparently storage size limit is right at 128GB though, from a quick search. So you'd have less after the OS install. Would also probably have more available replacement parts like batteries and expanded storage mods. Either way you are probably looking at something used.
I have a hard time imagining there also isn't an existing small market for mp3 players for secure facilities or for prisons that would have devices with the limitations you're looking for. Probably not nice prices or feature sets though.
Shockingly, if that market exists, it doesnt advertise itself. Otherwise they'd be making bank off the DoD and anybody else with restricted device policies.
Its not exactly a complicated device to produce afaik, either;