When we used DME in mid-June, we checked into BCV around 1ish, got into our villa at 2:30 and our bags arrived at 3:00. We completely forgot that the tip was already included and dh tipped the kid who delivered the bags.
As far as tipping the driver, I don't tip if he hasn't handled my bags. If I have just carry-on, as I did in June, than that goes on the bus with me. But, if I have baggage that is going to go under the bus because I am flying a non-participating airline, then I will tip the driver $5. When we were at Pop in August it amazed me to see how many people just grabbed their bags and went on their way, with nothing for the driver..not even a thank-you. That driver does a fair amount of work pulling those bags out.
I always have a carry-on bag with me...both for anything I may need at the airport and in flight, but also for when I get to my resort. I hate having to rummage through my big bags that I leave with Bell Services to grab a bathing suit, so I now carry that with me.