My pick would be, dealing with the ‘wild west’ atmosphere. That being, before cyber bullying laws existed, you had bunches of people getting off scot-free with telling you to off yourself or call you a list of derogatory terms.
First Gmail and then Google Maps were amazing. In a world where webpages looked like ass and any interesting technology required a plugin, those two apps were mind-blowing.
When someone in my lab told me about Gmail, I thought it would be a janky mess. How could a web page be good? But it was. It was great. It felt almost like a native app.
Then Google Maps came around. After MapQuest, I was expecting goofy tiles and weird hot spots to click on. Nope. They hit it out of the park again. Zooming in and out was… fluid.
Those were good days.
XMLHttpRequest had to be invented before GMail could exist.
But yeah, Gmail was the first online webapp that I personally used that extensively used XMLHttpRequest (aka: Javascript’s function for “automatically fetch more data from the server”)
Before that point, you wore out your F5 key waiting for new emails. Gmail comes out and “magic”, the new data just arrives because Javascript is hitting the F5 key in the background for you.