You have a few choices here.
1. Tag your bags and let DME take them. If your flight arrives, onetime, at 9pm, you can expect to be at your resort around 10:30ish. Your bags can arrive up to three hrs after resort checkin. You can have them delivered (depending on the resort) or ask that they be held until the next morning. If you do that, let Bell Services know, and then hang out the 'privacy please' sign on your door.
2. Don't tag the bags and go get them yourself. That will add about 15-20 mins to your overall time, but you will have your bags with you, which is nice.