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

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 Yes I know its my own fault for running outdated versions.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!

You could put a raspberry pi with a dac HAT together for a decent price (hifiberry.com). It doesn’t have a volume pot. If you want to see scope numbers on dacs look at this site.

https://audiosciencereview.com/forum/index.php?pages/Audio_DAC_Performance_Index/

I have been using iTunes for over 10 years and never had anything get scrambled, changed, or modified unless I did it myself. I have hundreds of CDs that I ripped 10 years ago and they are still the same as the day I ripped them. I never have to do anything with iTunes unless I rip a new CD. I can’t explain why you have this issue. 
Good luck in whatever direction you go. 

you are asking a lot of questions (good, but real answers are complex and lengthy).
You got great input on Audirvahna and Roon. I use Roon.
This is a sacred cow, but IMO cables are vastly over rated and over priced - difference or not, the money can be better spent elsewhere. yes you need a quality cable, with good shielding and the proper impedance. And good dialectic material.  pretty much full stop. I will now be crucified. I'm in good company.
DAC are HUGE.  As noted, its a whole topic but DACs perform timing, decoding, its a preamp, its a filter, its a [power supply... and all matter. IMNSHO opinion a lot.  Full disclosure i design this stuff for money (but its a side gig mostly for fun).
OTOH the law of diminishing returns is alive and well.  You can get a DAC that will kick the crap out of your tablet/laptop/PC's internal DAC for $99 - and its Made in USA (Schiit modi 3). But step up to $500+ and you get substantially better. Can you spend $25K?  yes. Should you? Well, is  Porsche GT3RS a nice plaything?  yes, it is. Is it the best cost/comfort/benefit trade off for an occasional blast through the twisties, or an occasional Autocross? Nope.  But god bless you if the $250k is not enough to stop the purchase. get two and drop one off at my place.
Do some reading and listening.  Go to Youtube and watch some stuff by Hans Beekhuysen. He's really good.  Kooky like most hgih end audiophiles, myself included, but good. And he does not subscribe to magic, which endears him to me.
Enjoy.  Happy to answer specific questions, but i avoid the endless opinion and flame wars that seem to occur regularly.
G