I like the idea, but I think society is re-discovering the same few problems again and again. The hedonic treadmill seems relevant here.

That we pay smaller prices, i.e. invest ourselves less in things, is a valuable observation though. Worse working memory, half-assing engagement, laziness, nihilism and the destruction of value, these all seem related.

The other factors have already been answered. If we consider where were are as 0, and where we want to go as 100, then we're always behind. Worse still is to consider the place we want to go as 0, because then we're in minus. In reality, what we have already is valuable.

Enjoy the process towards a goal and you'll have fun, enjoy only the goal and you'll suffer.

Another problem is literally getting used to things. This is solved in "The book of Est". Also partly by mindfulness, which observes rather than categorize every sensory impression into old models, so that everything is merely parsed (recognized as a hashed value), preventing change and novelty. The biggest sign that a thing has been reduced to a symbol and parsed is that you cannot reverse it. You can recognize a word when you hear it, but can you remember it if without hearing it? If not, that's a one-way association.

For the sake of efficiency, the brain might reduce all of live into a stream of familiar symbols, and discard anything which doesn't fit as "wrong". And you end up with a nihilistic person who is unable to change his mind or see value in things.

50% my own thoughts, so I don't have any more sources for you