Hi, Andy!
Three trips planned over the next year?! Wow! That's awesome! It definitely makes sense for you to purchase Annual Passes (APs). You'll love the perks associated with being a
Walt Disney World Annual Passholder!
You can actually go ahead and make your resort room reservations any time before your trip because you won't need your physical APs to do so. In other words, you can book your vacation before you actually purchase your APs and have them in hand. However, in order to receive the Annual Passholder discounted room rate, be sure to let the Disney Reservations Cast Member know that you would like to make your resort reservation using the AP rate (if available for your resort and dates).
When you check in at your resort, simply inform the Front Desk Cast Member that you intend to purchase your APs first thing the next morning. You will be asked to stop back at the Front Desk of your resort sometime during the following day to show your valid APs (otherwise, you will not receive the discounted rate). Since you likely won't have any type of park admission, you'll need to purchase your APs
outside the parks -- fortunately, this can easily be done at any Walt Disney World Theme Park or Downtown Disney ticket sales location. If you prefer, you can purchase your APs at the Disney shops in the Orlando International Airport upon landing, but you will receive a voucher that will need to be exchanged for an activated AP at a park ticket window or Guest Relations.
I hope this information is helpful to you, Andy. Wishing you a
magical trio of pixie-dusted Disney vacations! Please let me know if I can assist you further with any aspect of your planning.