I am single person and I buy the card. I usually have at least one person traveling with me, and when I went down last November I knew I would be getting at least 3 weeks out of the card. I don't drink alcohol, but my friends and family do, so it has come in handy at TOTWL. This is one place where I was able to show my card, but my friend paid with his credit card. Same at Coral Reef - showed my card and someone else paid. I am always prepared to have them refuse, and never take it for granted, but it is nice when they do accept payment from someone else.
I think it is very important to look at the various discounts available at the places you plan on dining. Most of the places I like to eat at every time I visit ONLY do TIW discounts - Mama Melrose, BOG, Plaza, Liberty Tree, 50s PTC, Sci-Fi, Garden Grill, quick service places at AK...
I really lucked out with this card. I purchased on Nov 27, 2015, and the cast member put 1/31/17 as the expiration. So I had a 9 day Nov/Dec trip, 5 days in March, 7 in May, 8 in September (some of these meals were with a party of 8), and will be back for 3 more days in November. And may try to squeeze in a long weekend in January