Sasha White is one of the best bespoke bicycle makers in the world. His Vanilla bikes have become collector's items - 15 a year and a backorder list about 500 deep. (it isn't that bad .. customers give up and sometimes die, so the real wait is probably closer to 15 years at this point. You start thinking about how long you will live and how long Sasha will be working.) He also supervises another line that builds 100 bikes a year and has a much shorter waiting list.
I know someone with about $40k spread across four bikes - none intended for racing. One of them is a $600 everyday commuter. He loves design, craftsmanship and perfection and notes this is much less expensive than a sailboat.
a tip of the hat to Kevin