This isn't the right attitude IMO. Yeah, you net lost money, but think of the hours and hours of enjoyment you got, the experience with different sound signatures, the times your favourite songs sounded so good.
Yeah, all of those past headphones won't sound as good now as your shiny new ones, but the money you lost was spent on the experience, not just the headphones themselves.
... Sorry, how i see it, if there is a possibility of a better experience, that is the best to get the sooner.
for example, i love ultrasone dj one pro, the only next step possible is ultrasone signature dj. there is no reason for me to buy anything else, i already know because i tested how the others sound.
like for source, i already know that hugo is the best for me. there is no real reason for me to buy other sources. I am buying other sources because i am not totally pleased with hugo price, i am still searching, but for headphones i already know what the best are.
i think that the journey is best done in a shop with a show-room, l;istening to every headphone you want, then pointing the best one and buying. if it does not hold out, rinse and repeat.
but this is just me, in Romania, i cannot sell headphones once i buy them, so... yeah... i might had liked your ways too if i was able to sell... but i cannot sell inside the country, there are around not many who love headphones, and outside, i cannot ship because to ship in another country i have to go in another city, i have to loose a day of work or school, it is a pain, and only the road to that city would end up costing me around 30$...
On the other hand, i am happy that i discovered that my end game headphones would be signature dj and ie800 iems. For now. i am going to listen to new shiny things when they appear.