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.
internet explorer sucked then and still sucks now
Microsoft hilariously butchered the introduction of Edge, which showed a logo that was strikingly similar to IE. They’ve sworn up and down that Edge wasn’t like IE. But Edge, behaved similarly to IE. It took Microsoft a few years to finally give Edge it’s own identity and more or less, better functionality.