Just because a flight is scheduled to arrive at 11 a.m. doesn't mean it actually will. Unfortunately, flight delays and missed connections are common. I consider any flight that arrives with less than one hour of delay to be "on time" from my perspective.
Use DME as designed: Attach the yellow DME luggage tags before you check your bags at you home airport and skip baggage claim at Orlando International.
Be sure to bring a carry-on with anything you'll need right away at WDW, as well as any fragile items, valuables, medications, and things for the first 24 hours in case the airline delays your bags.
If you head straight from your arrival gate to DME check-in (see the map in your DME packet), then you should be at your resort in 50-90 minutes after you get off the plane. Think of it as 70 minutes, plus or minus up to 20 minutes either way. It depends on how long it takes before your DME motorcoach is dispatched (could 1 minute to 30 minutes) and what stop you are (could be the 1st, 2nd, 3rd, or final stop).
If you don't use the yellow tags and you claim your own luggage instead, plan on an additional 30 minutes or so.
Finally, realize that check-in at your resort could take only a few minutes, but sometimes they get backed up and it can take up to an hour. Your room probably won't be ready that early, but you can get your GTTW cards, go off and have fun, and when you get to your room that evening, your bags will be in it.