Since I am already looking forward to the next trip i'll do the following:
Starting Points:
Hilton - 57k not including recent stay plus CC spend on my Hilton Amex
Hilton - Surpass weekend night free but won't include below
Barclays Arrival + - $140 in rewards
Swagbucks - $25
Quick Glance this will be the following plan -
5-Day Park Hopper® Ticket - $899.90 for my wife and I
5 Nights at the Hilton Buena Vista Palace - Book 4 nights get 5th night free - $149 a night with breakfast or $983.10 with resort fees or 130,000 points (73,000 as of today with my current stash)
For the fun part:
73,000 Points rounded up to 75,000 will need $25,000 in spend:
Manufactured spending:
50 GCS at 3.95 = $25,197.50 in "Spend"
Price Paid - $225 with MO Fees
Tickets:
Around $35,000 in Spend
Manufactured spending:
70 GCS = $35,276.50
Price Paid - $320 with MO Fees
Total Paid Out of Pocket - $545 for 5 nights/5 day hopper pass
Prices won't be exact since I also have a reselling side business which earns me free points but still around $500 for a Disney trip is fine with me!
Math will probably be a little off since I quickly did this but good luck