I've played the Gambler twice. Both times I have played it, I have missed the island left of the water and ended up by the 6th tee. Managed to par it both years and was the only guy either year in my 4-some to record less than a 7. The hole can definitely be a cardwrecker. To get on the island, the player must carry it 215 from the back tees and 167 from the regular tees. The island is approximately 100 yards long. From the back end of the island, the player has about 235 to t he green and about 135-140 from the front of the island. Taking the conservative route, the hole is 568 from the tips and 525 from the regular tees. I am yet to see anyone try the conservative route.
It is an extremely memorable hole but there are a few problems with it - primarily, it is terrible for pace of play between the water balls, the trip to the island and back (or in my case left of it), the photo ops every group takes, etc. It really can back the course up a bit. That said, I enjoy it, and it is probably one of the only holes down on the strand my buddies could tell you today exactly how they played it. Makes for great stories around a couple beers after the round. I'm not so sure it is great architecture, and I definitely wouldn't want one like it on every course, but once every year or so, I love it.
Mike