Because wine is so subjective to your own palate and opinion there is no straight answer to this, sorry. The long and the short is, it only matters to the person paying for it and the people drinking it.
Again, you don't have to spend a lot to get a lot. Stay in the price zone that you are comfortable in. If you are use to drinking $10 bottles then once in a while pop open a $15 bottle to see the difference.
Dropping $100 for a bottle is a big leap and yes it will make a difference not only in your wallet, but you will taste the different nuances that come with something of that caliber. Will you appreciate it more? Again, that's up to you.
If you are on spending spree and want to treat yourself to spend $100, in my honest opinion, buy four bottles at $25 each and compare them. Work your way up the ladder gradually. There are many bottles out there for under $25 that drink far beyond that price range.
Try anything from Spain and South America right now, tremendous values! France and Italy are coming back into the scene with great value driven wines again. The Rhone Valley of France has oustanding red and white blends for under $20 that are mind blowing and wallet friendly.
“People give me crap for trying to charge $125 for a bottle of Nagual del Judith (Caduceus’ high-end Cabernet Sauvignon), but they don’t understand it’s on the side of a hill, it’s under one acre, it’s all hand-farmed and there are only 50 cases of it. If I charge you any less than a hundred bucks, then I’m paying you to take it! A metaphor I use is, I think there are some fantastic musicians out there that could walk into Walmart, pick up an acoustic guitar and one out of 10 times give you something you’ve never heard before. But if you really want to make sure it’s all consistent, just go buy a Gibson Les Paul. There is a difference! There’s an absolute difference between an old vintage Fender and something that you order from Kmart, the craftsmanship that goes into it. In wine it’s no different; there are absolute different focuses and farming practices that go into the finer wines. The price goes up as the demand goes up, but the demand goes up, generally speaking, because of the art that’s going into it.”- Maynard James Keenan winemaker @ Caduceus Cellars, Playboy 8/23/12
A lot of factors influence price when it comes to wine. Think of it like this...if you buy a plain cheese pizza then it safe to say you're spending under $10 for the pie. Start adding bacon, peppers, anchovies, etc and not only do you change the price but you're also changing the flavor. Also, the more exotic the add-ons are then the flavors change drastically and the price really starts to climb. White clam pizza with white truffle oil is not the cheapest pie on the menu, but it's ohhh so delicious.
With wine it's the same thing. Start adding all the extras; oak aging, premium grapes, location, limited supply, etc and viola you're now up over $50 a bottle. A Cabernet Sauvignon grown in the Howell Mountain section of Napa is going to cost more than one that comes from Central Coast. Better grapes, location, etc. Likewise, pizza on Ferry St. in New Haven costs less than pizza made at Pepe's on Wooster St. Coincidentally they taste totally different too...the pizza that is.
Again, it's all about you. Be comfortable and confident when making your purchases, but once in a while treat yourself to something special without having to take out a second mortgage.
