We’ve done the resort switch a few times, but then again, we have our own car, so it’s much easier.
It also helps for you to plan for your room switch as you unpack and move in for your first leg.
I’d like to give different advice than Cleve just gave.
If you are including a meal plan, book the first package as normal with the exception that you buy your ticket for your entire length of stay, up to 10 days. Remember 10 days is the maximum length of an MYW ticket. For more than 10 days, you’d be better off with an annual pass anyway.
If you do that, book with a one day ticket and then use that ticket for credit towards the AP upgrade.
Book the second package as normal with one exception, book with only a one day base ticket. Now, hold on to that one day ticket and don’t use it.
That ticket is good for 30 years and you can use that ticket on your next trip for credit towards an AP or for additional options on next year’s ticket (i.e. park hopper).
Remember, in order to include the dining plan with your room, you only need to buy a one day, one park base ticket for each of the people in your room. You don’t need to buy length of stay passes.
Food for thought.
Oh, to comments about not getting into your room soon enough, there are ways around this too.
First, many times, your room is/will be ready much sooner than 3 PM. So you can always chance it.
Another option is to go to parks early and also grab breakfast.
Evacuate your first room between 11 AM and Noon. Now move to your new hotel and check in. By now it’s close to 1 PM and the chances are now 60/40 your room is ready. If not, head back to a park for a few hours.
Again, this strategy is mostly for those with their own car.
I can’t comment on transferring using guest services to move my baggage.