Good question. By and large I've never paid more than $15 for a CD. I always try to get them when they're on sale. That said, I'm willing to pay more for "rare" first pressings of classic LP's IF they're in excellent to near-mint condition. Inserts must be included as well if it contained them. Not all albums had them, obviously. It also depends on how long I've been searching for a particular release as well. There are many variables.
For example, in early 1991 I was browsing my local record store at the time and stumbled upon the original pressing of the first KISS album ( catalog # NB 9001 ) WITHOUT the song 'Kissin' Time'. I had learned that this version of the album wasn't available for very long, roughly for five months between Feb.-July of 1974. After this, 'Kissin' Time' was added to future pressings with a new catalog number ( NB 7001 ). The song remains on all current formats of the album to this day. Anyway, they wanted $200 for the "original", way out of my price range back then. And I didn't get to see the condition of it because I wasn't allowed to open the "re-sealed" plastic. However, I NEVER saw it again until November of 2003. I negotiated with a private dealer who had it in his collection and sold it to me for $50. While not "near-mint", it's in better condition than I probably give it credit for. It's been played, but well taken care of I'm told by more experienced record collectors. Especially considering how many hands it's likely passed through over the years. All in all, to this day I've never seen a better copy of it since. If I ever do, I would probably pay up to $100 MAXIMUM, again, IF it's in TRULY near-mint condition. In short order, it better look like it did in 1974 fresh out of the shrinkwrap!
Needless to say, I have yet to "stumble" on to one like that (

) ! But I digress. It's still Kiss' BEST album EVER, to my thinking. A timeless classic. But that's another topic entirely (

). Great thread.