In our town car service experiences, we really don't handle our luggage either. The only thing we do concerning luggage is to pick our bags off the carousel, but I would rather do that to make sure my luggage arrived in Orlando anyways. Disney and ME have nothing to do with your luggage arriving in Orlando, that is up to the airline company we fly with. I would rather see in person my luggage and know that it did not end up in Texas or something. Once we pick our baggage off of the carousel, we don't touch it until we are in our resort room. So, the few minutes I touch (and touch is all we do because our driver waits behind us at the carousel and as soon as we pick it off, he loads it onto a cart) my luggage at the airport is actually better for me, then I am not worrying about it until I see it (or don't if something happened) sometime later.

As far as time goes, last summer, it was about 1 hour, from the time we stepped off of our plane until we arrived at the resort. That included a 20 minute grocery store stop.