In the course of ripping a CD at a time, a person is not typically going to have 500 CDs to do (but wow, if that was some good music- WHAT A BARGAIN (that you fully own now)). Instead, they buy a new CD or 3 at a time or maybe get 5 or 10 as gifts... or at least that's how it went for me. Since it's not one gigantic job like 500 CDs but often just 1+ new CD, I've simply searched the internet to find a BIG size version of the cover (I favor 1500X1500 myself), correct any not square (to perfect squares) and then assign them to the new songs just ripped. Repeat when I bought another CD. And just keep doing the same as I buy CDs.
In a few cases, some of my CDs were OLD ones and a big version of the cover could not be found. In particular, some 1990's Rhino Greatest Hits/Compilations no longer had big-size images of the art, so I just made my own. In some cases, I scanned it on a scanner. In other cases, I considered taking a picture of it with an iDevice. And still in others, I just chose a generic image that fit the type of music (like a 1500x1500 British flag for 60's British Invasion "greatest hits" compilations). Again, it's no heavy load unless one is trying to rip a LOT of discs in one sitting. So today, about all of my 15K songs have large-size covers (or substitutions of my choosing) associated with them.
It's been the same with ripping movies from discs. That's also been an overtime proposition and I hand pick the "thumbnail" in a large size and also tag them with apps like Meta-Z and Subler. That would be quite a heavy chore if I was doing hundreds of movies in one sitting but the practicality of accumulating a collection is often maybe a few a month. If someone was doing 1 each week of each, they would have 52 CDs and 52 movies in one year... and 520 CDs and 520 movies in 10 years. It's quite easy work ONCE to do a disc or two (or even 4) each week.
Way to go on getting 500 CDS for only 20¢ each. Over many years, I've usually paid the "bargain" of only a couple of bucks for each one.
I’ve found that friends have stacks of cds in their attic space that they will away for free. I’ve got a couple more collections to pick up.. sadly it’s not always the best. I prefer complete albums as opposed to compilations.
I use this website for artwork which is quite good for general stuff but not so much for rare albums.
iTunes Artwork Finder by Ben Dodson
I was just reading your posts above about a NAS and how you sync photo albums which is good. I’ve become obsessed with having all my photos with me but I suppose realistically I rarely look at them. I think I might miss the automatic iCloud sync but I suppose it might keep my photo library more organised if it’s not syncing every screen shot