I'm not 100% sure but from all the posts I have seen so far this is what I have figured out.
If you don't do US Customs in your home Airport (ie Toronto Pierson) you will be clearing them in Orlando. (I did that part last year..so I know that is true)
You will have to get your luggage to clear Customs and put it on another conveyor belt which will take it to the Main Terminal/Baggage Clain...while you take the Monorail (

) over. (AT least you will know your luggage arrived with you)
Now is where the Magic Express is suppose to happen. You go down to Baggage Claim and look for the CM with the Mickey Hand and get directed to the check in for the bus to your resort. Your luggage is suppose to Magically get found and picked up by the CMs and delivered to your resort, eventually.
I don't know if they will let you take your luggage if you arrive really early...I guess you could ask if you can't fit everything you need for the day into your carry on.
Having said that, if you are arriving late in the day you should go get your luggage and bring it with you on the bus. (Seems to be what people are doing if they arrive after 5pm. And I have read that the CMs have also suggested that to some guests)
________
I think everything should arrive at your home 3 weeks before. But you might get part of it before that. I'm not sure if it depends on full payment being made first. (Would make sense that they want all your Money before they send you stuff)
Oh, and I think you are only suppose to get one tag per person...but you never know.
I will know the answers to all of these questions by Sept 3 since I will already be in WDW. And my final Payment is going to be made July 15 which is earlier than Disney requests. Which probably won't help anyone because you are most likely travelling before me.
Well, I thought I would try.