A few thoughts....
your tagged bags, that DME handles for you, can be expected in your room about 3-4 hrs after you check in. Room ready has nothing to do with it. If you check in at 11am, and your room is ready..terrific. You can take your carryon bag(s) with you and change in your room and head off to start your fun. If the room isn't ready yet, you can change in a bathroom, head out and start the fun.
Now, if you have your checked bags with you (meaning that you have not tagged them and gotten them yourselves at baggage claim) and your room is ready, you can go directly to the room, get settled and start your vacation. If the room isn't ready, you can still change in a bathroom, then leave your bags with Bell Services (Luggage Assistence) and then head off for the day.
And it makes no difference what time you arrive at the resort as far as luggage delivery timing goes...you can arrive at 9am or at 9pm....it will still take between 3 and 4 hrs to get the luggage. Of course, there have been reports of luggage arriving 2 hrs after, but that doesn't happen often.
Your bags, if taken care of by DME, will be brought directly to your room once they arrive at the resort.....even if you are not in the room. If you have left your bags with Bell Services, because the room wasn't yet ready, you will have to call them, when the room is ready for you and you return to the resort. They will then bring the bags to you, but you have to be in the room in order for them to deliver them to you.
What you decide is up to you. Many people just pack their carryon bags with anything they will need for the first 10 or so hours of their trip...that way they don't have to worry about bags getting lost, or delayed. They can also start their vacation right away with no wait for baggage delivery.
Other guests don't like not knowing if their bags got to MCO okay...so they choose to not tag their bags, and get them from baggage claim and then bring them to the bus with them. However you need to remember that tipping is no longer covered for baggage handling..either at the bus or at the resort level. It is only covered if DME takes the bags to the resort for you...in other words, you tag 'em with those yellow tags.
Just wanted to make sure that all bases were covered. Now it's up to you to decide what will work best for you and your family. Nothing is perfect for 100% of the people...what works for one, may very well be another person's nightmare!!!