I went mid May this year and here is when I did everything. I went with my sister who has two toddlers. When I started planning all I knew was I wanted to go in May and had it in the back of my mind.
Jan - ordered the 2018 DL Unofficial Guide, reread it and continued my love-hate feelings for the book. LOL
Feb 10 - Word got out DL tickets would be increasing that Monday (we usually have about a week's warning) so we bought our tickets that Sunday night to get them before the price hike.
March 15th- The DL onsite hotel discount for our dates were released (right when I was expecting them), so I booked a DL club level room at $465 a night plus taxes. I also had the option of a non-club room for $323 a night. I don't think I could have done better then those rates. Since it was a room only reservation, I could cancel until 5 days before travel if airfare didn't work out.
March 15ish - My 60 day dining window was open and so a week later I finally got around to it and I booked dining, weeks later I canceled and re-booked things and in the end used none of them.
Early April - Booked a deal on Jet Blue into Long Beach, (a much more relaxed and closer airport) for $126 RT each, we wanted Jet Blue because we were travel with little ones and wanted assigned seats. I don't think you could or should wait that long for cross country flights but I really recommend avoiding LAX at all costs.
May 1st - I noticed the off-site hotels were MUCH lower then I expected and some AWESOME last minute deals were starting to pop up, so I decided to start looking at switching.
May 6th - Booked my car from Costco Travel so we get the free additional driver perk Costco gives you, I paid $204 total for the whole time, I probably could have done better here?
May 6th - I booked a fireworks view 1 bedroom suite at the Embassy Suites for four nights, I paid $576 including taxes for the entire time and then got a $50 rebate from a credit card promo. The parking was $17 a night so that added a bit. I liked this hotel! We watch the fireworks from our picture window. It included a delicious breakfast and an evening reception with free drinks and free snacks and they gave us a nice bed for the baby. I called and canceled my DL hotel room one day before my cancellation window, the CM told me my room had already been assigned and I had been given a free room upgrade(!) in case that changed my mind, I hesitated, but stuck with our decision to have the bigger room off property for a fraction of the cost.
And that very next week we went, and our trip was completely magical, Long Beach airport is so small, the rental cars are literally right outside the front door. Crowds were all manageable, Paint the Night was the highlight, the snacks were yummy. The newly painted Dumbo had just opened and it is freaking adorable. We met Mickey Mouse. We didn't use a single dining reservation, because it didn't work with nap times. We went to Huntington beach, stopped and grabbed a bag of fast food, and spent a great morning there with the beach almost entirely to ourselves. There were plenty of restaurants in walking distance from our hotel that were frankly dirt cheap.
Was my planning TOO relaxed, yeah probably, but honestly, DL is such a different animal. I am so excited for you. Please let me know if you have any more question.