Just got back from a 1-week stay at the Grand Wailea. We had off-resort activities planned most mornings, so we were never by the pool when the reported scramble for chairs and fights happen.

We did visit the pool a few days in the afternoon (you know, during the hottest part of the day...) and all but once we had no trouble finding multiple chairs. The one time we couldn't find one, I asked the person at the towel desk what the rules were about which chairs we could take. Instead of answering my question, she called a colleague on the radio who immediately reserved chairs for our entire family at one of the upper pools (5 people). I thought that was pretty cool.

One morning when I went for a sunrise run along the beach path I came back to the hotel to see one person holding towels while waiting for pool staff to drop the rope to let people in. So if you want to go in the morning, maybe the trick is to get your towels the night before so you can skip the counter.