To give you an idea of what you would be getting, I looked at a menu from earlier this year. The wines, (and in one case, sake) are listed below alongside their reasonable retail price:
Taittinger Prestige Cuvee NV ($32)
Conundrum, California 2008 ($17)
Kanbara "Bride of the Fox" Gohyakumangoku Junmai Ginjo, Nigata (Sake) ($25)
Cru "Montage Vineyard" Chardonnay, Monterey 2008 ($23)
Lonardi Giuseppe Valpolicella Ripasso 2007 ($19)
La Crema "Los Carneros" Pinot Noir, Carneros 2007 ($16)
Mollydooker "The Boxer" Shiraz, McLaren Vale 2009 ($20)
Duckhorn Cabernet Sauvignon, Napa Valley 2006 ($55)
If you were to buy full bottles of every one of these wine, your total cost would be $207. If you assume that your pour is 3.5 oz of each wine, then you are getting 1/7th of a bottle. And for the sake, you are probably getting 1/20th of the bottle. So in terms of value, you are paying $60 for about $28 worth of wine, based on retail prices. Assume a 100%-200% mark-up for wine in a restaurant, and the $60 is a reasonable value. But none of these wines are wines that I would be excited about drinking with a meal of the caliber of V&A's. These are largely "supermarket" wines that don't appeal to me and as Rusty noted, may not be the best pairings. For example, I would not want to drink a Ripasso right before drinking a Pinot, irrespective of how well it went with the dish. LIkewise, I would not want a Mollydooker in front of a Cabernet. So for me, even at a "value" price, the pairings would not be worth it when I was trying to make a really special meal even more special. Feel free to disagree. It's only food and wine, afterall.
I do disagree. The wines aren't chosen simply on vintage, price point etc. They are selected to compliment the elements of the dish.
Given your particular tastes, you don't sound the type to enjoy wine pairings. If you feel strongly about the progression of the wine, basing that opinion on the grape/wine varietal rather than the wine itself, then you might not be the best sounding board for someone interested in pairings.
Restaurant markups for wine are upwards of 300% so you are most certainly getting more than $28 worth of wine. The pours are closer to 4 or 5 ounces, so you are getting 1/5th or 1/6th of a bottle.
A bottle of 2009 Conundrum sells at California Grill for $62. The average retail price is $21. That is a 295% markup, so V&A would safely be 300%.
Additionally, you would never be served a shiraz before a cab sauv. Those two wines are in the same tasting category.
From the WDW website V&A menu, with retail averages AND restaurant averages in brackets
Amuse Pairing
Pommery Royal Brut NV ($44/$132)
1st course (cold appetizer) Pairing
Bisson Bianchetta, Golfo del Tigullio (DOC) Génova 2007 ($23/$69)
OR
Domaine King Estate Pinot Gris, Oregon 2008 ($19/$57)
OR
Cîroc Vodka ($30/$90)
2nd course (seafood) Pairing
Mer Soleil Chardonnay, Santa Lucia Highlands, 2008 ($30/$90)
OR
Kanbara “Bride of the Fox” Gohyak umangok u Junmai Ginjo, Niga ta ($35/$105)
OR
Hyde Vineyard “HDV” Chardonnay, Napa Valley 2007 ($58/$174)
3rd course (hot appetizer) Pairing
Estrella Inedit, Spain (Beer, $15/$45)
Crū “Montage Vineyard” Chardonnay, Monterey 2008 ($20/$60)
OR
Ceretto Rossana Dolcetto d’Alba 2006 ($25/$75)
OR
La Crema “Los Carneros” Pinot Noir, Carneros 2007 ($31/$93)
4th course (entree) Pairing
Trinitas “Old Vine” Zinfandel, Contra Costa County 2006 ($35/$105)
OR
Lonardi Giuseppe Valpolicella Ripasso 2007 ($25/$75)
OR
Mollydook er “The Boxer” Shiraz, McLaren Vale 2009 ($26/$78)
OR
Duckhorn Cabernet Sauvignon, Napa Valley 2006 ($65/$195)
5th course (pre-dessert) Pairing
Quinta do Crasto Late Bottled Vintage Porto 2005 ($70/$210)
OR
I Vignaioli di S. Stefano Moscato D’Asti, Santo Stefano Belbo 2009 ($25/$75)
So, your progression wouldn't go from Shiraz to Cab as both are in the same pairing category. You would go from Champagne, to Pinot Gris, to Chardonnay, to Pinot Noir, to Shiraz to Port etc...mildest to strongest.
The retail price to purchase the 6 bolded wines is $291. The restaurant price to purchase the 6 bolded wines is $873. Assuming the pours are 1/6th of a bottle, a glass of each would cost $145.50. The retail price is $48.50. Therefore $60 is only a small markup from retail (123%)