Let's see if we can break it out of totals. That will end up being easier to compare in general (especially when considering the extra CS and deciding on VN/Sanaa). For the menu restaurants, I'm just throwing a general number in there with DDP style entitlements (drink, entree, dessert). Note, tips are not included in this, since they should be equal (or thereabouts) on both sides and cancel each other out.
(BeforeTax/AfterTax)
Kona (Oct) (No DDP): 35/37.28
Biergarten (D): 36.99/39.40
Boma (D): 39.99/42.59
Le Cellier (D): 50/53.25
50s (L): 25/26.63
'Ohana (D) (No TiW): 39.99/42.59
Via Napoli (L/D): 30/31.95
Sanaa (L/D): 30/31.95
CS (L/D): 13/13.85 (x3)
Mug: 14?/14.91
Snack (3 @ $3.50ea): 10.50/11.19
Buy TiW: $20 (your share)
DDP 5 Nights (Holiday): 56.94/night
So, a (very) rough estimate of each meal done. First look at the raw OOP:
(This is just adding everything up together except the DDP and TiW costs)
$373.29
Raw OOP w/o Sanaa/VN = $309.39
Apply TiW to the above where applicable (tax is after discount)
$210.44 (covered costs) + 110.24 (not covered) + 20 (TiW "cost") = 340.88 (Hey, I didn't do too shabby at guessing the menu prices
)
TiW w/o Sanaa/VN = 159.32 + 130.24 = 289.56
Apply DDP (use taxed numbers since DDP covers tax)
284.70 (DDP Cost) + 127.81 (Not covered) = 412.51
DDP w/o Sanaa/VN = 284.70 + 63.91 = 348.61
Now, you do have a couple CS credits left over, which would add ~$28 value to the dining plan (you can add $28 to the raw OOP values for comparison purposes). This brings it almost breaking even. However, you will be tied to the entitlement structure, which you've already indicated may not be ideal. As such, unless the value of prepaying and (more importantly) normalizing the prices between individuals is great enough to overcome the difference in structure and loss of non-DDP covered discounts, I'd shy away from it.
For the TiW, your personal "break-even" point (where the amount saved = the cost of the card) would be around $100 (1/5 of the normal break even). Anything beyond is pure savings. Since you've hit that mark with over $200 in discounted items, then you'll likely come out well ahead with TiW, even if the others in the party spent half as much as you did at the menu restaurants! (Note, even without VN and Sanaa, you'd likely come out pretty decently ahead in this scenario). You also gain the value of being discounted for the others at 50s, which won't affect your bottom line so much, but will work out nicely for those 5 others
.
(Even not taking that October Kona into account, you're still coming out on top!)
As far as DxDDP goes, you'd have to fit in at least 4-5 more TS meals as well as absorb a much larger front end cost. While I do enjoy it, it's not an easy thing to manage (plus, I go solo, so it's much easier to absorb the up front for me
). I'd suggest