Kimberly - based on your needs I would echo others and say the
DCL transfers are a no brainer - totally Seamless and you'll love it. You will put your tags on your luggage once you're out of the airport and in Florida and then once you give them to the bus driver, you will not see them again until they are delivered to the stateroom on day 1.... as far as leaving, they have porters greeting you at the bottom of the escalator as you leave the ship and they push a cart and you show them where your luggage is (You will get new luggage tags the night before the cruise ends to show you where to pick up the luggage) and the porter will put all of the luggage with you on the cart, push the cart for you through customs and then escort you back to the DCL bus and just tip him $10 or whatever you're comfortable with.
The luggage gets tricky at the MCO but we find sky caps are the fatest way to check the luggage, if you are flying SW you get dropped off at side B on the DCL bus and will have to walk across the airport to the A side, so it can be annoying but doable, especially if you pay $5 for one of those luggage carts that are available right outside of the bus
For those who rent the car - how convenient is it? How do you pick it up at the Dolphin and then you just drop it off at the port? Do you drop your luggage with the porters before or after you drop off/return the car?
for PP Meet and Greets tickets are like what another PP said, they are ticketed character events, free but they run out of them after day 1, so if you are interested in getting some timed character experiences, then be sure to pick them up at the port adventures desk on day 1, the line will be long but moves quickly, you don't need tickets to experience characters but we find them more convenient than following the character times in the navigator