Is there a good way to update album art directly on my ipod?

Hi, new here.
So I have an ipod nano 5th gen: 16GB.
I have ~1500 songs on it and have been facing a slew of interesting issues with my album art.
1. I prefer to add songs manually as I tend to want only some of an artist, genre, or similar, and I like the control it gives me. The problem that I've been having is that there is no efficient way to add artwork to the songs / albums on my ipod that I have ripped from CDs, and are already on my ipod. Going through all my songs and seeing if they have art would be tedious and time consuming, and the only better way to do this seems to be deleting songs off of my ipod and re-copying them. Normally, I would just delete all my songs and re-copy them all, and go do something else for half an hour or so, but there are some songs on my ipod that may not even exist on my computer anymore, and I can't get them again. Is there a better way to just synch songs with the ones in my library and update those that have had art added? (The synch button at the bottom of the ipod tab / window doesn't seem to do that.)
2. At one point, I tried manually adding artwork to albums using Wikipedia images / etc, and I know that many people like to put their own artwork for their albums. The problem I had is that adding the artwork directly to the album only updated the firts track, and the rest still had the big note on them. Is there a way to adress this and make it apply the picture to the whole album?
3. When I was finally able to update my images because they required an apple id, and I didn't have a credit card to give, the custom images on the albums stayed. Is there a way to override this? The artwork that was downloaded looks better then what I had.
I know this is a lot, but I think these questions are related enough.
Thanks in advance for any help!

See this older post from another forum member Zevoneer covering the different methods and software available to assist you with the task of copying content from your iPod back to your PC and into iTunes.
https://discussions.apple.com/thread/2452022?start=0&tstart=0
B-rock

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