Did My Disney Experience Kill Spontaneity at Disney World?

We took a "last minute" trip in July last year, booking at about 6 weeks out which for us is VERY last minute. My biggest advice would be to be flexible and to keep. Checking. The. App. If you have a restaurant you have your heart set on, be willing to eat at off times and check the app a couple of days out up until that 24 hour in advance mark when people are cancelling to avoid those penalties. Lounges are also great for a last minute trip because they are first come, first serve and you can normally order off the menu from an adjacent sit down. Landry's rewards membership may also be worth an investment. I think it costs like $20 or $25 but you get that back in a credit to use at one of their restaurants, and membership gets you a walk up table at places like Yak & Yeti quickly. Focus more on rope drops to get in those headliner attractions (get that at least 1/2 hr to 45 min before the park opens so you're a the head of the pack) vs. putting such an emphasis on FastPasses, and refresh refresh refresh in the app to snag some day-of FastPasses.

Yes.

My parents and I went to Hollywood Studios on a whim a couple weeks ago, we were able to complete all of the toy story rides. We did set up a DAS for Slinky Dog though but waited for the rest. I kept checking for fastpasses but nothing we wanted was available. Then we also went standby for Fantasmic. Even with the legacy fastpasses, we wouldn't be able to get on Toy Story Midway Mania with a fastpass unless someone gave theirs up. It really depends on your expectations when you randomly go.

Depending on the size of your party, try for 1 FP at time and keep adjusting times so they over lap. We have done great doing that.