I would only and have only ever paid over retail one time for a Birkin from a highly regarded reseller because there was no way I could ever find that color and leather combination due to both being discontinued.
In my opinion, nothing from Chanel is worth even close to retail now. I know that's not the most warmly received opinion by some, but the pricing seems to have egregiously outpaced the value. My mental benchmark for preloved Chanel pricing appropriateness is what I would have paid for it new in 2012-2015 or so. That's about the last time I felt their prices overall matched their quality.
In my opinion, nothing from Chanel is worth even close to retail now. I know that's not the most warmly received opinion by some, but the pricing seems to have egregiously outpaced the value. My mental benchmark for preloved Chanel pricing appropriateness is what I would have paid for it new in 2012-2015 or so. That's about the last time I felt their prices overall matched their quality.