To start off. I hate apple (won this iPad old job), and this is not helping. Anyway, I got all my music onto my iPad and it shows up in my iPad just fine, but when I connect it via usb to my TL I get a lot of artists repeating themselves. I have already went through all my music on itunes and made sure that all songs had the exact same spelling and everything on artist and album artist. I am at a loss I need help. If anyone has had this problem and found a fix or has any ideas please let me know!

 

What is the exact model and iOS on your iPad? I can test later with an iPad Pro (1st Gen).

I suspect that the older TL requires an older device.

I have a REALY old iPod Nano 4G for music with my 2009 TL.

https://en.wikipedia.org/wiki/IPod

 

I'm using an Iphone 12 pro and will have the issue you have sometimes. Usually it's when I switch to youtube and switch back to music. I unplug my cord and back in and good to go! Did you try the consolidate option in music/itunes?