My 16-year old DS and I just returned from a last-minute, 3-night, trip and I bought a Silver Plan package....we had a total of 12 wishes (2 per night per person)...
We used our wishes accordingly:
1 meal each at Alfredo's -- bill came to $110 before tip = 1 wish each (although the pamphlets and online said 2 wishes; we were only charged 1 ea.)
1 meal each at Fulton's -- wow, I had lobster and he had a special salmon dish that he loved...this bill came to over $135 (no alcohol) before tip = 2 wishes each (a 'deluxe' restaurant)
2 wishes each to see Cirque in Downtown Disney.
We would've used 1 wish on Rose and Crown, but I thought Alfredo's would be 2, meaning not enough for the other meals. Since we had extra wish each at the end, we used them to rent the water mice on our last morning!!!
These were items that would've made me think long and hard before bringing out my credit card individually, but it was great fun under the Silver Plan to just order what we wanted and eat where we wanted.
I agree that you may not want to use it for your length-of-stay....as much as my son admires a nice meal out, he got rather tired of HAVING to be somewhere for our PS each night.
I felt like it was a good deal for us, but hadn't really broken down the cost.
Have fun!!
