I’ve hit the 150-200 range, per single record, at least a few times now. Stuff like clean original pressings of Alice in Chains, Megadeth, the original press of "Into the Wild" soundtrack, etc. And several times I’ve hit the 80-115 range - e.g. very limited-pressing OOP Euro metal like Avantasia. Biggest single purchase was the Beatles mono box (recently), at 450 - worth every penny. The results and sheer enjoyment rendered usually make it well worthwhile - when the music content and sound quality both hit 9+ out of 10 for me, it's hard to back down.
Two notable dogs I’ve gotten in the upper price ranges were the 2006 MoFi Megadeth "Countdown to Extinction" reissue (sounds like crap compared to an original UK pressing), and that caramel colored Record Store Day reissue of The Sundays "Blind" (just impossible to listen to, as it doesn’t sound good). I wouldn’t pay $5 for those, knowing what I know now. But most of the rest has been justifiable.
Two notable dogs I’ve gotten in the upper price ranges were the 2006 MoFi Megadeth "Countdown to Extinction" reissue (sounds like crap compared to an original UK pressing), and that caramel colored Record Store Day reissue of The Sundays "Blind" (just impossible to listen to, as it doesn’t sound good). I wouldn’t pay $5 for those, knowing what I know now. But most of the rest has been justifiable.