Hi Matt:
Many Guests enjoy traveling to Walt Disney World when schools are in session since crowds tend to get heavier when schools are out of session. Most schools are generally in session during the first week of May, so you will likely enjoy more manageable crowds the first week of May. The weather will also likely be pleasant during early May, with the temperature likely hovering in the eighties. Early May is also a wonderful time to visit since the
Epcot International Flower and Garden Festival and accompanying entertainment will likely be running then.
I enjoy planning Disney vacations, so if this is your first visit, I would start lightly planning now. Read up on the Disney website and return to the panel to ask questions about Resorts, Dining, Parks, and Special Events. In my opinion, making advance dining reservations, which can be done up to 180 days in advance, is extremely important, so I would start planning your trip in earnest no later than about seven months prior to your trip so you can make sure you have time to research and plan ahead.
Enjoy planning and enjoy your vacation.