Myriad iTunes sync issues - song cutoffs - artwork problems - yeech!

Question

Hi all,
I’m running the latest version of iTunes on a (late 2013) Macbook Pro Retina laptop, and having several different flavors of syncing issues with my two devices –  a 16 gb iPhone 4S running iOS 7.1, and a 32 gb iPod Touch 3rd Gen running iOS 5.1.1.
As best I can tell, some syncing issues such as one of the ones I am experiencing (songs chopped-off when transferred and attempted to playback from the device) have existed in some way, shape or form for nearly 10 years now, so I’m not expecting any grand revelations here - but just looking for some honest advice on how to resolve in the shortest amount of time & with the least pain considering I have a fairly large music library in terms of syncing time required.  That being said, below bulleted-out are my current issues / frustrations / thoughts on where the problems may lie.   I would appreciate any advice:
Purchased iTunes songs (ripped MP3’s from CD’s that I own and tracks from other sources do not seem to have the problem…) play fine in iTunes on my laptop, but when transferred to either my iPhone or iPod, they will randomly (it’s not every track) be cutoff near the end of the song.  Sometimes the song will stop with 2 minutes remaining and go silent. Sometimes it will stop with 15 seconds remaining and go silent.  Sometimes it will stop somewhere in that time range and start the next track on the album while still displaying the info from the previous track.  The only solution I have found to this for purchased content thus far is to wipe everything out, and go back and download the tracks from the cloud.  I have somewhere in the neighborhood of 1000 tracks that fall into this category, so my options to download directly to the device an artist at a time are kind of time-consuming and cumbersome.  Would this have something to do with the file format of purchased tracks vs. ripped ones? I have a lot of older ripped material that was imported as MP3’s or MP3’s converted to M4A’s that never seems to have this problem.  The newer purchased files are mostly ACC’s which DO have the problem.   Also would this have anything to do with the fact that my library (including most of the purchased content) was recently moved over and imported to a new Macbook from a Windows backup?  Most of my iTunes library was Windows / PC for the majority of its existence for the past decade or so; we only recently switched back to Mac.
Discrepancies between deleting material on a device vs. what iTunes recognizes when it is plugged back in:  The other day, being frustrated with the random song chopping, I deleted everything on my iPod Touch 3rd Gen by going into Settings, Options, General, and “Usage” and then “Edit” and selecting to wipe out everything in iTunes. The device appeared to do this, and I was showing 28 gb or so free out of 32 once it completed.  Great, right?  I proceeded the rest of that day to painstakingly download approx. 900 tracks from the cloud onto the device, hoping to correct the chopping issue.  It did this, and I still had roughly 10 gb free. Great, right?  Later that night when I plugged the iPod into my Macbook with the 30 pin to sync, iTunes on the laptop for some reason still recognized the songs which I thought I had deleted hours earlier and showed me multiple copies of everything.  For the ones that had been deleted, when I clicked to play them on the iPod through iTunes, I got the little gray exclamation point - ! – in a circle like when a track has moved libraries and cannot be found.  iTunes then told me my sync could not be completed due to being over capacity on the device by a ridiculous 12 gb or something like that. Huh?? I could have gone through and manually deleted the (by that point more than 1000) duplicate tracks and synced to have made room I suppose – but after accidentally hitting Autofill – iTunes threw up its hands and would not let me do anything further.  Any attempts at that point to delete either pending Autofill tracks or missing duplicate tracks just led to endless spinning on the “Preparing Update” notice on the device which led to me having to kill iTunes.  Can you say big-time frustration?  I eventually opted to restore the iPod to factory (iOS 5.1.1) settings and start over.  That device is currently at home slogging through the process of attempting to re-download 400 some songs from the cloud over wi-fi so that I can avoid the cutoff track problem.  The plan after that is to sync playlists for certain artists over top of the purchased tracks so that my ripped tracks can merge with them to round out the playlist. Do you see how this is beginning to become a marathon?  
Last but not least - it seems to be just since the last few iTunes upgrades for Mac, but I’m having a huge problem suddenly with album artwork staying synced properly. After one recent manual transfer session (30 pin between the iPhone and the Macbook) roughly half of the tracks I transferred had mismatched artwork.  Doing this through the cloud (downloading tracks “Not on this iPhone” via the iTunes app) doesn’t seem to have the same problem, but of course this takes longer. Also, what is the deal with “Show All Music” in iOS 7 and playing tracks from the cloud?  This is a really cool feature that allows you to save a ton of disk space on your device, but I have found that when I do this that many tracks have mismatched artwork.  For example right now I’m listening to a Grateful Dead song that is displaying Genesis artwork.  Huh?? Artwork is less of a big deal than the track lengths being chopped off, but it’s still annoying.
iTunes revolutionized the music industry and on the whole has been fantastic.  But it seems as if lately, little irritating problems like the syncing issues are becoming more and not less prevalent, and the problem is they aren't being dealt with.  I got my first Mac in college nearly 20 years ago now, and have been generally entrhalled with Apple products ever since.  But I have to say that this kind of junk lately is more what I would expect in the vein of problems from the shoddy-PC world that seem to linger and never get fixed.  Cupertino folks - what's the deal???

Answer 1

You're not the only one judging by the forums!
Likewise I have been using Apples since the Apple IIe(!) and have found them great in every respect. iTunes however over the past couple of years has deteriorated to th point of being unuseable. Apple has made iTunes the hub of your digital life and so it really has to work seemlessly.
I currently have had to completely wipe and re-install my 64Gb iPhone 4s several times to get my music back on to it. I cannot het any playlists to sync which is really annoying and it generally undermines my faith in Apples software quality.
Please put whatever resources are necessary to fix this soon Apple or you will certainly start to haemorrhage customers to other platforms. After all if iTunes remains broken then what's the point of paying the extra for Apple qulaity? You may as well uplaod ebverything to Google play and be done with it!