Giving up on Itunes! Alternatives? I want to run my hardrive with a dedicated tablet.

I gave up on iTunes a few years ago and went to Spotify. Easy to use and you can use your iPhone or iPad. 

The OP is right about iTunes/Apple Music's disorganization. Everything looks organized within iTunes itself but if you look at the folder structure in iTunes Media within the Music folder at the Finder level you'll see that the original album structure has been completely scrambled. Individual music files, regardless of format or the album they originally came from, are scattered across multiple folders in a structure only iTunes can navigate. That's all fine if you want to continue use only iTunes/Apple Music for playing from your Mac but if you want to use an application like Audirvana or JRiver you're out of luck. Both those will show that same complete jumble of music files and albums.

Dacs do not need to be hugely expensive. Audiosciencereview.com (ASR) has shown that there is almost no correlation between price and performance when it comes to Dacs. Use the component browser on that site and the reviews to find a dac with good performance at a price point you are comfortable with, and you’re off to the races. 

I have looked at the iTunes music file at the finder level many times and my files are all well organized. My album structure is not scrambled but is in alphabetical order under the artist name. If you have an album with multiple artists, than the album can be placed into a compilation folder when ripped or each individual artist in the album would have its own folder, whichever you choose. 

There is a separate folder for artwork and there are two .itdb files and one .itl file. These files keep track of song ratings and how many times a song has been played. These files can simply be recreated if missing.

I can see where this arrangement can be a problem with Classical music, but I don't have any Classical music.

Thanks For all the info guys! Awesome wealth of knowledge, Gettin some good advice. So a dac is what we used to call a soundcard in a computer, and presumambly an outboard dac offers better performance than those in most computers and phones. I remember when digital was just coming out guys building dedicated towers to run their digital. One thing I noticed is that most outboard dacs have pretty traditional circuits, caps and resistors, so that looks good to me.

So I mostly listen to digital stored on hard drive through a macbook, old os, old itunes, definitely contributes to my problems, but i'm not the kind of person to get the latest thing and spend money on updates and whatnot that will be obsolete in a year, wish I could tell you that was gonna change, but it's not.
Basically my itunes refuses to read some file names, images and metadata, puts songs in wrong albums or removes album names periodically, creates and modifies playlists and albums including their name and artist, so i spend hours manually inputting information only to have it scrambled. Yes I know its my own fault for running outdated versions. I'm sure it's great for most people and if it works for you more power to you! I'm looking for something simple that won't do things without being directed to do them. Also the interface is junk. Has anybody scoped these various players to see if there are any differences or done listening comparisons on the same system?Also anyone building dacs with boards, I'd be more interested in that than most of what I see out there. When the device producing the signal has a volume pot on it it doesn't fill me with confidence. I come from an era when hifi meant separating signal from other circuitry as much as possible, especially power! So I wont ever be using blutooth, wifi or streaming, Only direct connections to the component making the signal.
It sounds like the dac's  in affordable ranges are all pretty comparable, and the players are mostly archiving tools and controllers? I'd love to talk with someone who has built a few dacs to hear about their experiences and what is actually affecting the sound, and get some tips on building one from a sound card. Any thoughts on tablets? Thanks for all the info, You guys are saving my butt!