Digital player for truck suggestions

@elevick I would probably aftermarket both the car stereo and speakers. The company offers a $500 Bose 7-speaker upgrade package, but I doubt I would be happy with that And would be happy to spend more if it got me more.

And no $100K SUV; we're looking at a $32K pick-up at most. 

@simao

Start by ripping some CDs into an ALAC or AIFF format into iTunes on your Mac. Stay with AIFF or ALAC format because FLAC isnt compatible with iTunes. Pick your favorite CDs.

Sync them to your phone and play them via either bluetooth or with the audio/audio adapter on your iPhone depending on the iPhone model. Enjoy for awhile knowing you’ve spent zero $ to do this so far. Not counting the truck stereo. :)

Maybe get a Tidal HIfi subscription and use Tidal’s download feature to add music  to your phone via home wifi for playback later. This is a great way to listen to music not in your library. Heck, you could bag the CD rips and just do this but I’ll bet there’s an artist or two whose music you like who isn’t on Tidal. So there’s that.

Then, think about a player with lots of memory that’s compatible with Tidal and wifi and will hold a lot of your rips and Tidal tracks. An iPod Touch with, like, 128G of memory. Maybe something else but it has to have an operating system compatible with adding streaming apps like Tidal and plenty of memory.

But right now, you have everything you need to get started. Except, maybe, the connecting cable/adapter to the aux input.

Keep on trucking baby.

Some automobile manufacturers offer WiFi connectivity service - I think GM does, and that allows you to stream music for playback on your audio head unit. I don't have first hand experience but technically this functionality should allow you to listen to Tidal HiFi (via subscription) in your truck/car. Not sure how the data usage charges are calculated.

@simao I would be absolutely stunned if any current vehicle came without a USB port and the capability to play digital files from a flash drive.  I wouldn't spend any money until I learned the capability that's built-in.  You should also have the ability to connect your phone via Bluetooth or a cable from the headphone jack (using the aux input), assuming your phone still has one :).  I personally wouldn't get THAT worked up about sound quality.  Unless your sitting still with the vehicle off, I doubt you'll hear much difference.  I use FLAC in my main system but convert them to 256 kbps mp3s for the car and they sound fine.

Regarding aftermarket replacements for the Bose system that comes installed - you may find that it's near impossible or at least VERY expensive to do so.  I have a 2013 Honda Accord and the sound system and multi-function display are completely integrated into the innerworkings of the car.  I'm not sure it could be removed and have the car still run.  They wouldn't do this on purpose would they??? :)

Dick

Simao & DJohnson,
I just completely reworked a disgusting Bose system in my Infinity.  If you want to talk about complicated messes...this wins.
1-Bose BLOWS.  When we ripped out the speakers, we found that there wasn't a single tweeter in the whole vehicle.  Bose has now invented the newest audio bullcrap a "Twiddler".  I kid you not.  This doesn't go as high as tweeters and is definitely not a mid range.  They figure that since the amp/head can't reproduce full frequency responses, why try.  Thanks Pandora & XM for continued low fidelity.
2-Did I say Bose Blows?
3-The bose amp was terribly underpowered.  Even though we had dual subs, there was nothing to push them.
4-Most car USB ports are crap.  Not only are you stuck using the built in DAC, you are usually forced to use MP3/MP4 or similar quality.  Any of us that have tried to use flash drives in cars will testify to how unreliable this can be.
My friend Chris who is an installation genius did have some solutions.  First, Alpine, Rockford and a few others make very nice processors that actually work in line with the factory unit to take out any lame bose equalization to get you full flat frequency repsonse.  This is an intense install that is an all day job at a shop and will run $600-$1000.  If the processor doesn't do it for you, you can always add an amp or two (or three...).  DO NOT SKIMP.  Many car audio amps are full of hot air.  My Class D Alpine puts out real wattage.  
Replacing factory speakers may help but just how much???
Sorry to rant :-)
Go see an aftermarket installer to see what they have to say.