Dracula wasn't defeated in a generation. Rogue Legacy is a heavily Castlevania inspired game where you explore through an evil shape shifting castle. While you only play as the successful Belmonts in the Castlevania series, surely not every generation was that competent, and in Rogue Legacy you play through all the generations that didn't make it...
Pro Player does not loose purchased loot
The upgrade system in Rogue Legacy works by spending the money you gained in the last level (you lose all your money when you start a new one), with upgrades passing down through generations by being either upgrades to the family manor, or family heirlooms. This way even when the player dies (which happens a lot) the player will not loose their purchased items allowing them to continue without starting completely over.