I've used DME about 5 times now....my average time from plane to resort checkin line is about 70 mins. Shortest time was at POP..got there in under an hour. Longest time was 85 mins...again, at POP. But that time we were the last rather than the first stop. 70 mins is a good average.
The line at the DME counter is fast moving..so even if it looks lengthy, it isn't. And only one person per group has to be in the line. The bus line wait can be very short but can also be closer to 20 mins. Depends on when the bus leaves. If you get there just as your resort bus pulls away, you could have a 20 min wait. But I've been one of the last on the bus and then the bus pulls away.
Luggage is to be expected in your resort room up to 3 hrs after resort checkin. I have two personal experiences....at BWV, I checked in at about 1:00 pm, was able to get into my villa at 4:10 pm, and my luggage was at the villa door at 4:25. But, at POP in January ('08) I checked in at 11:00 am, got into my room at 11:15. I didn't expect my luggage to arrive until 2ish. But it didn't get to the room until just past 4 pm! There is a long story here, I won't go into it. I usually just checkin and drop my carryon in the room and then head to a park. Didn't do that this time...paid the price so to speak.
So, this brings up another point...be sure to pack a carryon bag with anything you may need for the first 6 hrs. of your trip. Luggage can get held up....see my above experience. And yes, sometimes it can be misdirected..usually by the airlines, not DME. DME does a terrific job of getting our luggage to us in a timely fashion. But sometimes 'stuff' happens. It's a good thing to have some small toiletries, a swim suit, change of clothes, and park passes in a carryon bag..just to be safe.
All this being said...I love DME, I love the ride to the resort, I love not having to worry about my luggage. I love that it's free, sort of.