I do them just about every trip, sorry don't make FPs that early out and have an AP so don't do packages. As far as is it too much trouble, obviously not to me since I do them often. It is easier with a car since you can transfer your luggage yourself and even pack two bags if you want. I always drive down and according to my mood, I either pack two bags or use packing cubes and just pack for that first leg in a cube and put the dirty clothes back into that then in the back of my car instead of back in my luggage.
What I do as far as moving: I get up early even on vacation so I get up early, go for my walk, get ready and load up my car then call and check out of resort #1. I drive to resort #2 and go ahead and check in. Chances are my room isn't going to be ready but they know I'm there and I'm not picky about location or view so I just tell them I want first available. If I'm staying at a moderate, they normally know which building the room is going to be at I go park the car there and leave my luggage in it and hop on a bus. If I'm staying at a deluxe, 9 out of 10 times, I'll take my luggage to bell services and have them store it while I go to a park. The reason I do this at the deluxe resorts is the parking tends to be a little further out and I don't want to go back to my car and lug it to the room after I've been at the park. I just call down when I'm back and my room and have them bring it. When I get the text that my room is ready it depends on if I'm ready to leave the park or not as to whether I go to the room.