There truly is very little bad or ugly with DME/RAC. But, it's good to know the particulars, so you aren't surprised by anything.
Your bags will arrive at your resort, up to 4 hrs after resort checkin....resort checkin, not MCO arrival. I'm seldom around to see when my bags arrive because I'm off at a park having fun or in the pool swimming. Bring what you will need for that first day, in your carryon bags. That way you can change if need be and start your fun without having to worry about checked bag arrival.
Didn't realize it was after resort check in and not MCO arrival, but that still shouldn't be too late. We are bringing a carry on, and after we check in at the resort, we plan to walk over to Jambo House and grab some dinner at Mara, explore the resort a bit, and maybe go for a swim.
If you are arriving later at night, after 9:30, be aware that DME does not provide baggage p/u and delivery after 10pm. You either have to get your own bags or wait until the next morning to have DME move them from MCO for you.
Doesn't apply to us as we arrive at 3:25pm, but I did know this.
For the return home.....for a flight departure time of 1pm, you will have a bus p/u time of somewhere between 9:45 and 10:15. Be at the DME bus stop, ready to go, at least 15 mins before the time you are given. That time is the time the bus leaves, not the time you need to arrive at the stop!! I would get the bags checked as early as you can..then head off and get some breakfast. Don't wait too long because the lines get longish.
I'll try and get there around 7:30 at the earliest, 9 at the latest. We are doing EBCI, so no problem with the boarding passes.
There have been a few reports of bags not making it to the home airport but they were delivered the next day. I think that may have been a result of the newness of SW participating and having more bags than usual to get to MCO and possibly someone waiting too long to check their bags.