Yup. I'd watch the map and then suddenly poof - gone. One time the app said the driver was 7 minutes away and it looked like that on the map but then 30 minutes later no Uber had shown up for me at the front of the resort and they weren't on the map anymore. Guess they cancelled the pickup?
Second time I tried it the times kept changing and I could see them on the map but they never got near the resort and never showed up.
That's a very strange set of coincidences, and it's very hard to figure out what happened from your description -- even for someone who's given more than 1,000 rides and taken several dozen as a rider. But I'll try to give some ideas on what might have happened.
First of all, all of what we're talking about is based on the driver's GPS (which is usually Google Maps). The driver's position can be off considerably when the car is moving, and if we're on an expressway, it can be WAY off. I have arrived, waited, and then called or sent a text, and have the rider respond that the app just told them I was 5 minutes away. (I've had that with both Uber and Lyft -- it's a gps thing, not an Uber thing).
The ETA problem is greatly magnified when the pickup point is inside a large complex like a resort, and it can get really crazy if there are barriers like security gates.
Second, your first situation sounds like you ordered the ride from one place in the resort and then went to the front of the resort when you anticipated the driver to arrive.
The big problem with doing that is that the pickup location is the point where you
ordered the ride, and that is where the GPS tries to take the driver. I once had a ride request placed from the deck of a cruise ship docked at Port Miami. The pin was in the middle of the channel, and the location was shown as "North Atlantic Ocean!"
If the driver goes the point where you ordered the ride and you're not there, or they can't get access to the pickup point, they will probably cancel the ride as a "no-show" and you'll be charged a cancellation fee.
Uber has a new feature on the rider app which allows the rider to
move their pickup marker if it's in the wrong place. They also allow the rider to share their exact location,
if they choose. Why Uber makes showing your actual location
optional is a mystery to me, but it is something a rider must
affirmatively do -- and I've never had it happen yet.
Both times I did the text thing and never got a response.
It's really hard to tell, but it sounds to me like both of your rides were probably canceled no-show. You can call or text a driver while they are en route, and you can contact a driver after dropoff at your destination -- because you left something in their car, for example. (Lyft only offers phone contact)
But if a ride is canceled, no text or telephone call will go through after the cancellation. That's true with both companies.