I've always contended that Leupold scopes are overrated. I've owned quite a few of them over the years, and I have never felt that they were worth the asking price. Simply stated, there are a number of comparable scopes that are just as good for less money. I think Bill hit the nail on the head with his comments. Growing up, I believed Leupold was the best because it was on the cover of all the magazines. However, once I got old enough and a little coin in my pocket, I found out that it wasn't necessarily true. Once I was able to actually try different scopes on the range and in the field, I found that the Leupold wasn't all it was cracked up to be. I have shot VXIII's on the bench next to Burris, Nikon, Sightron, Bushnell Elites, and Cabelas Alaskan Guide scopes, and have found the Leupy to be no brighter or clearer. In fact, I have found that the Leupold lags behind these scopes in terms of optical sharpness and clarity, especially at dusk to dark. I would have never believed it, especially considering the VXIII is twice as expensive as some of the other scopes I have shot it against. But, I have seen it with my own eyes on more than one occasion (and have had other shooters agree). Does that mean Leupold is a bad scope? Not at all. One of my favorite deer guns wears an M8 6x42. But the simple fact is, there are better values. Its even more pronounced at the Rifleman and VX1 level of scopes, which are jokes.
I will say this, though. It's ultimately up to the shooter to find what they like best. I've shot and hunted with guys who are content with Tasco's and the like, while I've shot with others who consistently spend more on their optics than the rifles they are mounted on. Personally, my most expensive optic is a Trijicon ACOG, which cost close to $900 when I bought it. My cheapest? Probably a $75 Simmons on a .22 rifle. Each serves their purpose, and they both get the job done.
Are expensive optics worth it? Yes and no, and it's up to you to decide.