I guess the problem for me is that by and large, "aspirational" trips just don't exist. I'm happiest at either (1) an HP/HH with a few nice restaurants on the same block or (2) something in the Hyatt Regency ballpark (possibly Hyatt/Hyatt Centric as well) with a decent on-site restaurant. TBH I don't feel terribly comfortable much "above" that tier (the only real exceptions being...honestly, the Royal York and Queen Elizabeth in Toronto/Montreal, respectively, and those both have a history as solid railroad hotels more than anything).