So, we tonight, created our own version of this:
5:00pm - Left our room at BLT to board the monorail to Poly
5:20pm - Arrived at Trader Sam's where we enjoyed 2 glasses of wine, two signature drinks, the fried potstickers ($53 event)
6:40pm - Left Tambu Lounge to walk to Grand Floridian Cafe for dinner
7:00pm - Arrived and checked in at Grand Floridian Cafe
7:20pm - Seated at Grand Floridian Cafe where we ordered 2 glasses of wine, a caesar salad, and two entries ($80 dinner)
8:40pm - Left Grand Floridian Cafe to monorail back to BLT
8:58pm - Arrived at Top of the World Lounge where we ordered 1 glass of wine, 1 signature drink, and the 7 layer cake ($38 event)
9:00pm - Watched fireworks / Holiday Wishes
9:30pm - Returned to our room in BLT
So, our 4.5 hour progressive dinner included 8 alcohol drinks (4 per person), 1 appetizer, 1 salad (shared), 2 entrees, and 1 dessert. It cost us a total of $170 or so (with tips at 15-20%) and we were able to watch the fireworks from the 16th floor of BLT vs. 4th of Contemporary. Not quite half the price of the scheduled event, but close (understanding we ate the cheapest option at Grand Floridian).
While it is a cool idea, it can definitely be done cheaper than the given rate and we didn't have any monorail wait issues. Walked onto a waiting monorail at BLT and had to wait about 5 minutes (but got on the first monorail) at Grand Floridian. And that's in prime dinner time while the MK is open until 12:00a (and the ride from GF to BLT was during prime "return" time for fireworks at 9pm).
All-in-all, the concept is good and the cost isn't terrible, but we enjoyed being able to go to the actual bars (especially Trader Same's) vs. a special place / area and spend less without any issue.