While i haven't owned the top-echelon of jeans like $450 Pure Blue's, i've owned many a pair of "high end" jeans (7/citizen/ernest sewn/apc/made & crafted/etc). All of them were between $2-300, and none of them were ***that much*** better than the levi's i wear now. Plus I can own 3 different colors/washes/fits for the same price, which drastically expands my wardrobe.
I have this discussion w/ the owners of a couple of my fav Toronto shops (for example, Lost & Found, which IMO is the best new store in the city) and they stop stocking expensive jeans since Levi's transitioned the Capital E cuts to their normal Levi's line. It's the same thing w/ Chino's... why pay more when Unis makes amazing ones at a much better price.
Anywho, I've had this argument before. It's all personal preference, and my preference is to not spend $300 on jeans when I can spend $100 and get very similar fit/cut/quality.