I was a Mac user through those years and it wasn't roses during much of that time. In 1998, Microsoft had Windows 95/98 which didn't have the nice polish I loved from my Mac, but it was a modern OS running on much faster and cheaper hardware. Mac OS 8 was really good looking, but it wasn't a modern OS - cooperative multi-tasking and no separation between processes. Mac OS 9 didn't change that.

At the same time, Intel was just demolishing the PowerPC. You could get a much faster Windows PC for a third of the price. Yes, Apple has a price premium today, but it's marginal and you're usually getting better stuff. Back then the price differential was huge.

Things didn't get better fast. Windows XP gave home users Microsoft's NT OS while Mac OS X was so slow it was basically unusable. Windows apps would start up instantly while OS X would let you watch an icon keep bouncing in the dock. Intel kept pummeling PowerPC both on price and performance.

You started using OS X in 2003 so you never used 10.0 and 10.1, but it was painful. Even in 2003, performance was still slow and compatibility could be hard, but it was getting substantially better. More apps were fitting in with the OS by this time. A lot of the early ports from Mac OS Classic weren't very good and the UI elements didn't always look right.

OS X did give Apple a big advantage: it was a Unix with good laptop support. This brought a lot of techies to the platform. But it's hard to say that Microsoft wasn't doing well for most users at this time. Windows XP was so fast and the hardware was so cheap.

Microsoft did have some fumbles. Windows Me should never have been released. Windows XP had a lot of security issues for a while. But most people weren't even looking at Apple - until the iPod.

I think Apple's resurgence was their own doing. The iPod got people interested in Apple again. I think delivering a laptop-friendly Unix brought a ton of techies and developers to the platform. I think the move to Intel processors closed a huge performance gap that had been plaguing Apple.

Even today, while Apple's Mac business is doing great, how much of that is attributable to the impact that iOS had? Even then, Windows is still the vast majority of the market (85-90%). Most people never saw a reason to leave Windows.

If Apple hadn't gotten hit products like the iPod and iPhone, would we have seen the same huge resurgence in the Mac? Or would people continue buying faster Windows machines at a third of the price?

I'm a big Mac fan, but there were some painful days in there and 1998-2005 could be pretty painful. It wasn't all bad. Mac OS X was getting better by 2003-2004. But there was a lot that wasn't so great. Still, I know people who did switch then. Windows could be annoying as hell - but it didn't start being annoying in 1998. Windows 3.1 was very basic and Windows 95 would have all the same complaints as Windows 98. But Windows 95 was so much better than the Classic Mac OS. Windows XP was more usable than the early Mac OS versions. But OS X started showing promise and it was getting fans - and many were pissed off with Windows.

But I don't think that's what gave the Mac its resurgence. The iPod and iPhone brought users who wanted Apple's experience on their computer.