I think more money = better only up to a point. And that "point" is very low WRT headphone amps. I say this because headphones are, relatively speaking, ridiculously easy loads to drive and headphone amplifiers are ridiculously simple devices needing very few parts.
Audiophiles tend to think of headphone amps as mystical magical devices that take the hand of your headphones and lead them in a complex and sophisticated rythmic dance. Bull#%&@. Its an electrical device that takes an incoming signal and makes it bigger. Sure you can talk about feedback circuits and output impedance - and they will affect how the headphones respond to the amp, but thats all "circuit 101, stuff for an amplifier builder. The person designing the amp simply has to decide what the parameters will be and make it happen.
Its the consumer who has to read between the lines, separate fact from fiction, and decide which amp to buy. That consumer can choose to spend whatever amount they want, just like they choose based on looks, build quality, power ratings, intended impedance load (headphones), etc.
I have no problem with someone spending $2000 on a headphone amp. I just hope they are doing it with their eyes open to the reality of what they are getting for their money.
PS: I still have not had a chance to see or listen to the HDVD800, but for the record, I do think it is a well engineered, high quality piece. Now the WA7... Thats a different story...