IPod displaying wrong album artwork; connectivity issues

Question

I have an iPod Classic 80GB, model #A1238. It's a little over 2 years old. I use it on a PC with Windows Vista. And I am currently using the latest version of iTunes.
My iPod is pretty much at full capacity (music only!)-- if I want to add something, I have to delete something else. Lately, a lot of the new music I add displays the wrong album artwork in my iPod (even though everything's correct in iTunes). Usually, the recently added songs/files displays the artwork of another recently added album... but now, my recently added albums are displaying artwork for other, "older" and random albums in my iPod library! It's driving me crazy since my iPod is so neatly organized!
I have a feeling it has something to do with syncing? For the past year or so, I have had issues connecting my iPod to my computer. From time to time I get one of those "this device can perform faster" messages. That sometimes leads to other error messages about not being able to eject my iPod b/c the "device is in use," or I get an excessively long period of syncing or "verifying" my iPod. When those things happen & I'm stuck in a certain process, I typically try manually ejecting the iPod... and when that doesn't work, I restart my iPod.
In fact, I've been restarting my iPod a lot these days. I try to restart it every time I'm about to plug it into my computer to remove/add new music (I figure it might not have issues with wrong album art if it gets kind of a "fresh start!"... and that only works some of the time).
So what do you think the problem is with the album artwork?!? It seems so trivial, but it really drives me crazy-- I really love looking at the artwork, as silly as that may sound! I've heard that I might have to restore my iPod back to factory settings, but I'm REALLY hesitant to do that-- I have about 16,000 songs on my iPod & to get them back, I'd have to re-import my many, many CDs! It will probably take days! I'm also afraid I might start having the same old issues if I start getting those error messages about the device performing faster (I feel like all my little complications arose from those issues).
Some things to keep in mind: If it's not clear already, I manually manage my iPod's music library-- I don't sync entire libraries or playlists or anything. And most of my album artwork is downloaded automatically when I import CDs or purchase music from iTunes. Once in a while I manually add the album artwork (like, I find the album art from the Internet, copy it, right click my song files on iTunes, select "get info" & manually paste the image in the artwork box). That sometimes helps, but those files can still sometimes display incorrectly in my iPod, ditto song files purchased from iTunes (though more often than not, I don't have issues with those files' artwork).
Lastly, is it bad for me to be repeatedly restarting my iPod?
Any help would be much appreciated!! (And be forewarned: I am NOT too tech-savvy!)

Answer 1

The only way to get things resolved will be to restore your iPod. Since, as you imply, you've been manually managing your iPod and not keeping copies of your media on your local hard drive, you will need to recover the content from your iPod before you restore. There are plenty of threads here detailing just how to do that. If you haven't got the space then you will need to start, I guess, by buying an external drive big enough to hold all your media in one go.
Your iPod shouldn't need resetting on a regular basis. For myself I found that when I had a large number of playlists on the iPod (basically everything in my library at the time) it was more likely to freeze when playing games or even moving around the menus so I cut down the number and complexity of those I put on the device which seemed to fix things.
tt2