We will be arriving fairly late on a Saturday (8:30 PM), so what are are the odds of getting our luggage that night?
Because of that uncertainity , we are considering hiring a limo and do a grocery stop. Will we find a grocery store open? (I'm guessing around 9:30 PM).
If your flight arrives, ontime, at 8:30, you should be at your resort by 10pm, could be sooner. Your bags will be picked up by DME workers if you have tagged them. Then, you can expect them about 3 hrs after resort checkin...by 1am. But again, probably before that.
If you go the DME route, I would put in a grocery order with wegoshop.com or gardengrocer.com. Yes, they charge a delivery fee, but it's around $15ish, then they deliver to your resort at the time you have requested.
If you decide to use a towncar service, it should run about $130ish, not including tips. You will have to wait for your bags...so you won't be getting to the towncar until about 9:00ish...takes about 10 min to get to baggage claim, and then 20 or so mins to get your bags...again, could be sooner.
You then take the bags out to the car. Head to a grocery store...by now it's about 9:30ish. You get out of the grocery story around 10ish, and to your resort by 10:30ish...could be sooner depending on how long you spend in the grocery store. Lug everything up to your room.
I guess it all depends on what kind of experience you want. I would prefer to either tag my bags (if arriving prior to 9:30) and have DME deliver them to my room and then have put in a grocery order, or....leave the bags untagged, take them to the DME bus with me (with tip in hand for the driver for stowing your bags), and then have them upon arrival at the resort...and use a grocery delivery service.