I just sat down to figure it out now. We normally stay DVC, but my husband has a meeting at the GF in the fall, so we're going to stay using the convention rate they offered.
5 Nights Grand Floridian – Outer Building, Garden View, Convention Rate $1232
- deposit $247, paid using points on Chase Sapphire
- balance to be paid with Disney GCs purchased using Target GCs obtained from rewards programs
2 RT fares on Southwest PHL - MCO
- paid with RR points; 9/11 fee paid OOP = $22.40
2 5-day park hoppers, purchased through eBates/Orbitz @ 10% back; purchased May, 2013
- paid $637, got $64 cash back from ebates and 1274 points (worth about $12.75) on Chase Sapphire
Food budget - $1000 (6 days/5 nights) ~$200/day
$50 Shula’s GC – paid $41 on Raise .com
$50 Wolfgang Puck GC – paid $47.00 (also purchased on Raise)
$140 Landry’s GCs – from rewards programs (mainly MyPoints) + $25 Landry’s Select Birthday Bonus
$40 Starbucks GCs – rewards programs (KelloggsFamilyRewards and RecycleBank)
Taxis, airport parking and misc. expenses ~$200
Total expected OOP for this trip = $22.40 + $637 - $64 +$41 + $47 +$1000 + $200 = ~$2K
Of course, we'll bring more because there's always SOMETHING that comes up and messes with the budget. Several years ago, my husband tore his Achilles tendon while in Disney and we had to cancel dinner in the castle. We had to pay for it anyway because it was a last-minute cancellation. And then, we had to pay for room service on top of that! Yep, there's always an unexpected expense!
Well, that trip is over and the numbers are in! My husband invited another couple to join us. That's a whole 'nuther story that is better left untold. However, it did cause for a lot of changes to my plans.
First of all, we ended up putting the remainder of the hotel costs on the business credit card for tax purposes. $985 OOP as a result of this move.
I added Early Bird Check-in to our Southwest tickets at a cost of $25 apiece for RT. That's an additional $50.
We got a shuttle to take us to the airport and home. Cost was $110 with tip.
We rented a car, using points to cover the cost. But we had to pay for gas and tolls. That added another $60.
Then, we decided to valet park the car two nights during the trip for another OOP cost of $25/night plus tips. Add another $75 to the OOP costs.
I ended up taking an 8-night trip with my sister the month before this trip, so I redeemed a DVC AP voucher that I hadn't been able to use the prior year. I got sprinkled with pixie dust when the CM allowed me to redeem the voucher without paying an additional amount (the voucher itself expired on 12/31/14). My husband used a couple of days from an old no-expiry MYW ticket and I bought him a 2-day after-2 PM convention ticket for the other days. OOP (without considering the AP or MYW pass costs - yes, I know that's cheating but the costs were already sunk) was $86 after using Disney Visa Rewards Dollars to pay for part of the after 2 PM ticket.
I ordered Finish Line Party tickets, partially paying for them with Disney Rewards Dollars for an OOP cost of $43.50.
Once at the Food and Wine Festival, I purchased two Sampler Packages for a cost of $125.67, which was paid for with a Disney GC earned from rewards programs. Actual OOP cost was $0.
We never ate at Shula's, Wolfgang Puck or any of the Landry's restaurants. I did buy a couple of beverages at Starbucks.
I used the rest of my rewards Disney GCs to pay for all of our food with the exception of Il Mulino, where we spent $135 cash for the two of us (including tip). At least they validate for parking, which would have cost $18 for self parking at the Swan.
Our return flight was delayed 2 hours, which meant having to purchase dinner at the airport. Just sandwiches and a couple of bottles of water for a total of around $15. I also used my Starbucks card to get coffee because for some reason, I was freezing in MCO.
Overall, the trip cost us about the same amount OOP as I had anticipated, but the numbers got moved around quite a bit. So much for planning! Like I said, something always comes up and it's best to have extra money available to cover it.
) This gave us 600.00 in gift cards and 150.00 in reward money from our visa... total of 750.00 fun money for our trip!! WHOOO...HOOOOO! 
) Curious if you find TiW worth the additional cost. My calcs says yes for my wife and I (because alcohol is included 
)..........what do you think?
New York city is very expensive 
