Been to WDW many times but these are most recent trips:
Our trip in January 2011 8 nights 5 BLT 3 Parent's vacation house 2 adults 1 child
$518.20 r/t airfare for 3 from JFK to mco on JetBlue (had a $65 credit)
$800.00 for 5 nights in a studio at BLT renting points (eBay listing was $850 but got it down to $800 after cash back programs)
$899.00 for 5 nights of deluxe dining plan for 2 adults and 1 child (paid using Disney rewards earned from Disney Visa)
$501.20 for 2 8 day park hopper tickets (used mousesavers discount at
undercover tourist plus upgraded at park and had a ticket for DD already)
$1000 in gift cards earned and gifted for spending money
3 nights at my parent's vacation home
1 week rental car for $45
Additional oop $300
Actual money spent from our pockets: $2164.40 (not including earned and gifted gift cards)
Our May trip 2012 *7 nights 5 at the Dolphin 2 at BLT 2 adults 1 child 1 infant
$350 r/t long island to mco for 2 people and 1 lap child. DH flew free for his conference
$366 including tax and fees for 2 nights at Dolphin pre conference stay
$475 total for 3 nights of conference (DH just had to pay this for myself and DD as DS was free, and that isn't per person! His company paid the rest and as you can see we got our $475 worth and then some), for 3 nights at the Dolphin with 3 meals a day including an amazing Universal dinner at Hard Rock Cafe, admission to Islands of Adventure and private lavish party at Wizarding World of Harry Potter, $100 dining credit at Disney World, 1 day after 2pm tickets to Disney (used 1 but saved the other 2 to use on our next trip)
DH's company paid for our airport parking as well as transportation to and from the airport and Dolphin
$410 renting points for post conference stay 2 nights at BLT in a lake view studio
$389.66 for 2 nights of deluxe dining plan 2 adults 1 child
$1500 in Disney rewards and gift cards earned and gifted
$905.04 2 adult 1 child 7 day convention park hopper tickets
Actual money spent from our pockets: $3195.70 (not including earned and gifted gift cards)
Our upcoming Christmas trip 9 nights 2 Beach Club 7 Dolphin 2 adults 1 child 1 infant
$75 for r/t flights long island to mco for 2 adults 1 child and 1 lap child for fees and early board (signed up for 3 cards for Southwest visa when they had the 50,000 points and qualified for companion pass for DD)*
$1421 12/25-1/1 7 nights at Dolphin including taxes and fees
$181.75 for Fantasia 2012 NYE dinner for 2 adults 1 child
$149.61 breakfast for 2 adults 1 child at CRT
$75.59 for 2 adults 1 child Tomorrowland Terrace Dessert Party
$320 for 2 nights 12/23-12/25 in a studio at the Beach Club renting points
$389.66 for 2 nights of deluxe dining plan for 2 adults 1 child
$555.86 for 2 adult 1 child 6 day park hopper tickets ($955.86 using mousesavers undercover tourist ticket discount then another $400 cash back from my BOA card offer)
$1490 for $1550 worth of Disney gift cards for spending money (plus*we will have $350 in earned and gifted gift cards)
$155 for 3 night SUV car rental
$50 for 1 day SUV car rental
$100 for upgrade AP Florida resident (my license is from Florida)
$100 Tables in Wonderland
$40 upgrade for DH and DD's tickets
$0 2 after 2pm 1 day 1 park tickets (leftover from DH's conference)
Actual money spent from our pockets so far: $5103.47