ITunes got smarter about album art, why not the iPod Classic?

I'm a long time iTunes fan and noticed that iTunes USED to be "stupid" about album art where the user had to paste the art in multiple times (into every track) or it didn't display in cover flow properly.  And, once you did this, then a synched iPod would also display the correct album art on every track instead of SOME of the tracks, which I saw it do...
But the latest versions of iTunes have noticed got "smarter" and I have seen it now where you only need to paste in one image, and iTunes displays it as needed AUTOMATICALLY on all other tracks on the same album.
This is obviously a step forward, especially if you have 5,000 tracks on your iPod!!
I just got a new iPod Classic and I have concluded after a lot of technical research and experimentation that it is still "dumb", and seems to need the album art pasted into every track STILL.   It's annoying to me as a computer scientist that the same feature or benefit isn't there on both platforms.
I know this is a pretty advanced question compared to the normal iTunes user, but I was hoping that someone could point me to a better solution than having to paste up to 5,000 album arts into my iPod?
Thanks in advance for any help, I appreciate any comments.
D.

As a computer scientist I love your handle!    Are you real?  <jk>
I go way way way back with iTunes, I was using it to rip CD's, and as my primary music player on my desktops and laptops beginning in the 90s when it was Mac-only!  Long before the iTunes Store even appeared, in fact.  I don't actually have even one purchased iTunes store track, just have 5,000 ripped files from my own purchases.  I also have edited the files I've imported, so my collection has only stuff I have pre-listened to and like personally, so I found Shuffle play to be a "100% win" and I use it exclusively on both my laptop and my iPod.  It's a "100% win" because I stack the deck, to use an american expression.
I had a large CD collection of 500+ CDs so you can see I am a major music enthusiast.  Unfortunately, I don't possess the CDs any more but I do have the electronic copies...
I loved how ITunes was time-optimized algorithmically to high efficiency in the ripping process (no doubt Steve Jobs guidance) and automatically looked up track names and artists on the Internet, and automatically managed the MP3s files too.  It's competition (Winamp and WMP) still required you to manually manage everything.  I also used the burn mp3 cd's function which made single-button burning of up to 12 hours of playlisted content a LOT.
So, that's why I do recall the early days when it was not as "smart" as it is now.
I visited your scripts page, a lot of very cool things there, but, if I understand correctly, Visual Basic doesn't work on OS X?  That ***** MICROSOFT.  Reminds me of when MS didn't support Apple clients on Exchange!
Any further suggestions?
D.

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