Love this idea! Where do you usually stay?
My favorite hotel is the dolphin for price/location, it's great for walking to epcot without dealing with waiting for transportation and it is more adult than the disney values for about a $100 a night premium which to me is worth it. I am a gold elite Marriott member(hopefully will hit Platinum this year) so I get bonus points(which translate into reduce costs for future trips) and free room upgrades(internet/balcony/view). My plane tickets round trip are $200 on spirit airlines where I also get points as a saver club member to be applied later. If AP ever comes back then I pay once a year for tickets but currently I am using the military salute 5 day park hoppers which are $300.
With all the discounts and cheap airfare it's not that bad, again, comparing it to owning another property with taxes, payments, and upkeep. Not to mention I can not leave for 5-6 months, I need to be back for family/pets.
If I wanted to really cut I would get a hotel off property for like $80 a night, with AP pass and $200 airfare, that's only like $1,500 for 10 days(including a $50 a day food budget) in florida with full round trip tickets. You could easily get that down to $1200 if you order garden grocer and have a few simple lunches/breakfasts.
I basically goto WDW every 3 weeks from Oct-May, many times don't even step on a ride just walk around or relax at a resort on a laptop, because I know I will be back anyways. The more I go the more I understand how to stay away from crowds/when to take a break back at resort, when and where to get the best snacks, and all the little secrets about the park. I am an avid Disney Food Blog reader, Touring plans, and watch all the big youtubers to continually maintain my knowledge of the parks.