I've never won the opportunity to buy a bottle of Pappy 23 ($300) so I've never pondered spending that much before. I'm sure if I did win that rare opportunity, that I would part with the bills. I use the George T Stagg rule, which to me is; if a bottle of GTS costs $98 retail then how much better is "X" whiskey costing twice or three times as much and is it worth the gamble? Like you I put extensive research into even the inexpensive whiskies, so usually I have the answer to that question with minimal effort.