You have to add in the cost of sales tax (6.5%) to get the total actual cost. Also, the Tasting Sampler also includes a "Limited-edition 21st Epcot International Food & Wine Festival trading pin and lanyard." You can subtract the cost of that out if it's something you would consider buying. I collect pins so it might be worth it to me (after I see what it looks like.) Limited Edition pins regularly go for $10 to $15 and lanyards at the Disney Store are usually about $10.
Here is how I would calculate the value per item of the $59 Tasting Sampler:
Total Cost = $59.00 + 6.5% Sales Tax ($3.84) = $62.84
Subtract Value of Trading Pin & Lanyard (say $20.00) = $62.84 - $20.00 = $42.84
Divide by 8 Items = $42.84 / 8 = $5.35
A similar calculation for the $109 sampler gives a per item price of $6.01. Since I took the $20 off the total of each, the $59 sampler actually provides a better value. Buy two $59 Samplers and you get 16 items, PLUS another pin and lanyard!
If the pin and lanyard are worth more to you, then the value of the sampler goes up. If it's not something you would buy, then the calculation changes.
And I think the prices at the booths already include sales tax, so if you can find 8 items that cost more than $5.35, it will make sense.
Does this make sense or am I missing something here? Would love to know as I'm going to be there in October.