Caldera was the one with the graphical installer where you could play Tetris. I believe Mandrake was the one that was very similar to Red Hat (back around RH 5.2) but I remember it being a little easier to get working.

X was difficult. I remember sound being fairly easy if you had a sound blaster or turtle beach. The modem and PPP was where I always got hung up. I finally bought an external modem and that made things much easier.

Hmm, I didn't remember using PPP or a modem. Now, I remember why.

At work we had a LAN. At home I had a Windows 98 box that talked to the internal modem and dialed up, which routed to a special orange ethernet cable with the wires crossed to an emachines box in the second bedroom. That one had dual boot linux on it for tinkering and thought it was directly on the internet. Good times.

Installing Mandrake 9.2 (2003?) was in many respects better than installing Windows XP. The graphic installer was incredibly smooth, it had a real integrated partition manager (something that looked like Paragon PM), and a much more accurate estimate of expected time. If you had old enough hardware, everything would just work perfectly. I still have fond memories of Mandrake.

For Red Hat the big jump was with version 6.0. The earlier release, 5.2, still had the text based installer. But still, I do remember looking up the horizontal and vertical frequencies in my monitor's manual :)