I think a lot of the bourbon market is built on mystique as well as supply-demand. when i first got into bourbon, i thought 150+ for a blantons was worth it all day. Once i finally got a few and tasted it, it's not worth more than SRP. Too much variance between bottles, and not really deep. Same thing with eagle rare and buffalo trace. good bottles for SRP. now when you get into the BTAC line or special releases like the Elijah Craig barrel proofs (back when they were pushing 13 year age statements), Birthday Bourbon, Russels 15... etc, i think they're worth significantly more. those are GREAT pours with tons of depth.
HOWEVER
at the end of the day, preference is key. a buddy of mine LOVES buffalo trace, while I can't stand it. I really love george T stagg but it's too hot for him. everyone's preference is different.
I've also become disillusioned by the secondary market, to the point where I've learned what my palette leans towards, and have gone there on the readily available list. what i mean is, i love wild turkey (Russell's specifically) and on the Heaven Hill side it's Elijah Craig specifically. so my daily drinkers are Elijah Craig toasted and will dip into the barrel proof sometimes, and Russells reserve single barrel with an occasional sip into 13/15/single rick.