What we do:
1. Buy one set of tickets that covers our entire vacation (usually from
Undercover Tourist).
2. Book the resort reservations as room only unless we want to do dining plans, in which case Disney requires you to book packages. The packages can be ticketless (you used to not be able to book ticketless packages with dining unless you were booking an AP holder or
DVC member reservation. However, I understand that you can now generally book ticketless packages with dining but this must be done over the phone).
3. Make ADRs for each resort reservation starting at 180 days from the first check in date, then at 180 days from the second check in date, etc. (you used to be able to do all of your ADRs starting at 180 days from the first check in date, but generally not anymore).
4. Link your tickets on My Disney Experience, and make FP+ reservations starting at 60 days from the first check in date (these can be made for the entire trip).
5. You will get a set of magic bands for each resort for everyone in your party (unless you opt out). We pick a specific color for each person in our party (mine are all blue, DW's are all red, etc.) so as not to get confused. Each person's bands can be used interchangeably (we bring at least a second band for everyone as a backup).
6. Whatever band (assigned to you) you choose to wear will generally only be active for one resort at a time. So, as I understand it, once you check into your second resort, everyone's bands are no longer usable at your first resort. This can be an issue, for example, if one person takes bags to the second resort and checks in while other family members are still back at the first resort.
7. We use bell services to transfer our luggage on resort transfer days (and then head to a park, etc., as usual).
8. One area that is still somewhat unclear to me is when you have dining plans at both a first and second resort and try to use dining plan entitlements on the transfer day. Obviously, if you haven't yet checked into the second resort, you'll only be able to use credits from the first resort. But, I'm not sure about the situation where you still have credits left over from the first resort and have checked into the second resort. In that situation, I'd guess the credits would come off the second resort stay since that is now the active resort. In any event, I'd try to avoid this situation by using all of my first resort's credits before checking into to the second resort.
The most difficult aspect for me is the discount game. I try to hold out to book my reservations until after room discounts come out (assuming they do) because waiting can only help my odds of a discount (plus, I don't have to call back later to try to apply a discount). But, because I have my heart set on a specific combination of resorts, I'd rather have a reservation at rack rate than not get one at all. So I have to constantly monitor Disney's website to see how my intended resorts are filling. If room categories start to fill up at a particular resort, I'll go ahead and book that resort at rack rate (I'll still try to later apply a discount if/when it comes out).
