We have been covering as much as possible.
All of our accommodations for all three trips are already paid in full (May, October and December).
Airfare is purchased for both May and October (Jetblue). Looking at Westjet for Christmas to avoid the added cost of exchange.
Annual passes for Universal were bought in early November, not to be activated until May. It was really my planning OCD that got me moving on that one, but it seems like a genius move now.
Ditto on the PhotoConnect AP.
Food budget for May is 100% accounted for. Working on October's trip now. We have a villa with a full kitchen for each of our trips, so we can dine in to save if necessary.