Digital media server/players for a Skeptic?

With all due respect, honestly it sounds like this isn't the hobby for you. You sound like nothing is worth the trouble. With audio the devil is in the details. If you don't believe in "all the audio hoodoo", don't even bother to understand what format your digital music is in, then what point would it make for anyone to try to give you advice about the differences between various server solutions? What good would a nice server do for you if you won't even be able to sort through your untagged library? I am sure you won't be happy to hear what most here think of mp3 sound quality.
If you want to learn how to tag your files, there's plenty of assistance here. Same with understanding file formats for iOS, windows, etc. Hell, we could spend all day debating the definition of "good, cheap wire", but it probably isn't worth your time.
Sorry to be so callous, but I am being honest.  Cheers,
Spencer

Oh come now. I can’t be the only one here that thinks spending more than $20 on a USB cable is a waste of money and has some actual technical background to understand why. A lot of the stuff sold in the hi end audio world is comically ridiculous.

I’m a EE by training and have been a musician most of my life. I know what a piano sounds like and having a bass player in my ear pretty intimately, or what a cymbal’s shimmer sounds like because I’ve played nice ones often. I also know what it sounds like to hear music in a studio setting and then listen to it at home. Probably a lot of you do too.

I took my time researching and picking out the system I have and enjoy quality on a budget that makes sense for me. And I'm not immune to picking through details to improve it within reason.  I might not own the yacht others here have but I can still enjoy my time on the water!

I welcome opinions of those who might know more than me. I’m not opposed to rescanning the music I own on CD. I use mp3 because it fit on the portable players I’ve owned. I like to run so I’ve probably owned 20 iPods of every era.  If you think I’m beneath you because I won’t buy a Pono then sure, don’t waste your time. When a Pono can pass a double blind comparison to an iPhone, I’ll take a listen...

I really don’t know a lot about digital media devices. Some seem excessively designed and very expensive for someone with a < $5K system . Maybe some are not and would be a good fit for me.

. I don't think it should be necessary to be an IT expert to have to enjoy listening to music.  I have the Bluesound system, which is a Server and a whole home system.  It isn't entirely hassle free but is a lot easier that computer audio, which I've given up on after few years of Mac & DAC .  Bluesound has a reasonable sounding built in DAC but I use it's Opticl output into my Mytek Manhatten.
  Merging your prsent files into Bluesound is more work than just ripping CDs but if you buy from a dealer who knows how to do this and will be available to answer your questions it makes it a lot easier

Thank you.  So bluesound is basically storage and management of the music files, but the mytek does all of the decoding?   

Can one skip the dedicated DAC and just go direct into a receiver's optical in from bluesound? The mytek's pretty far out of my budget.

What do you need to do instead of reripping? 

I probably should re-rip all my CDs to flac anyway and create compressed files as needed for my ipod.   The tags are a mess and I've yet to find a tagging tool that isn't totally junk.  I've tried picard, tuneup, and a few others.  I have a ton of compilations and loads of really old MP3's.  The apps crash at anything over a 1000 files, which makes for a lot of manual work to feed them in.  Although I might look for a service to do them in bulk.  I have a lot of cds!

THx again

Personally I find most of them overpriced when you can build your own 2TB Linux based music server for about $600 and get iPhone/Android app support..

If you are using the digital outs of your airplay I do think you'd benefit from a Wyred4Sound Remedy reclocker, as would Google Cast.

I rip everything to FLAC, but download some DSD as well, and use USB 2.0 to play to my DAC.

I'm not sure if it works with iTunes, but PS Audio's LAN rover is also a good solution, but again, $600 seems so pricey to me.