If I won the lottery, I imagine buying an extra large Golden Oaks home and then letting Liners stay in the extra bedrooms for free. (I can’t imagine they let people rent these homes anyway!)
Also I think I’d start a vlog where I’d see how many times I can ride one specific ride per day. Like… 17 rides on Space Mountain by park close.
What Disney-related stuff would you do if you won?
I would buy another DVC contract so both boys could have one. And pay the annual dues until they expire.
And then go each year.
Sounds great! If I had kids, I am sure I would do the same for them!
Great idea. When I was giving DVC some thought 18 months ago, even though I am a senior citizen, I figured, well, my 2 kids could share it. They both declined the possible opportunity because they didn’t want to pay the dues. I did not buy DVC, but if I won the lottery, that could work!
A home in Golden Oaks has been my thought as well.
Whenever I saw your posts, I figured you were a UofI grad born in '74 … now I realize you are a '74 UofI grad 
You are correct.
I would do a World Tour of ALL the Disney parks and go first class all the way!
I would do a World tour of all the Disney Parks and Disney Cruises!
Start in California and take the cruise through the Panama Canal to Florida and then the Trans-Atlantic to get to Europe. The Asian parks, I guess I would have to fly…
Ooooo good idea!
I’d do more DCL, but I don’t think my WDW trips would be more frequent. I’d still stay off-property, but I do think I’d do more TS and character meals.
I’d work in another DLR trip, for sure. 
Why stay off-property? You wouldn’t be interested in the benefits of on-property transportation?
EDIT: Then again, you could just have your butler drive you 
I like spreading out in a house - we are a big family. And I like my own transportation. In over a dozen visits we’ve ridden the busses once from MK to HS and back to “hop.” It was awful.
I mean -maybe- I could/would stay in some luxurious spread in Grand Floridian or such, but then I’d be sharing pools… nah. I like a house.
But à chauffer would be cool.
If I’m dreaming, it might as well include club 33…
I would stay in the World for a year, maybe 2 weeks in each resort 
…
Would also make a list of ALL attractions, shows and tours to be sure to try every single one. Same goes for the restaurants.
I’ve been lucky enough to benefit from a friend’s membership of Club 33 several times.
I’d join if I won the lottery for the following very specific reason. The clubhouses provide (generally) quiet, cool oases of calm right in the middle of the parks. They’re a chance to get out of the heat and humidity and chaos and just chill out for a while. Maybe have a drink and something to eat — no ADR required, of course. And visit beautifully clean toilets with toilet paper so soft you could use it for bedding.
The clubhouses themselves are not particularly spectacular. The one at AK is fully purpose-built and only recently opened, and I haven’t been there yet, but the others are all repurposing of other rooms. They are nice, for sure. But so are lots of public access places at WDW — but those tend not to be in the parks themselves.
The ticketing and VIP tour perks are nice but I honestly think you lose something if you just whizz from ride to ride without ever really having to wait.
Love that idea!
Nice to get the inside scoop! It does sound lovely. I’m sure I’d add that to my bill
You’ve mentioned a few times on the boards that you don’t have many close friends (or something along those lines), but you have had a friend take you to Club 33 more than almost every other Liner … so maybe it’s just that you choose your friends wisely
Am I the only one who would stay in one of the $3,000+ per night Polynesian Bungalows? I’ve always thought they look very cool.