I started with a C64 when I was about 5 years old, which was wonderful at that time. We had a nice collection of games bought from a local store, and later a huge library of games stored in a shoebox, copied from and shared with other neighborhood kids.
A friend up the street had an XT because his father worked at IBM, and then a 286, then a 486 I think. He was also the first person I knew who owned a CD-ROM drive (external, 1x speed).
We eventually swapped our C64 out for a 386SX IBM clone, as they called it at the time. Installing MS-DOS 4 (4.01?) on it ourselves from floppies failed repeatedly before we finally got it to work. Our 386 was pretty unreliable for the first year or so, and had to be taken back to the computer store where we bought it several times. It was all worth it to play the Indiana Jones Graphic Adventure though, and many other awesome games after that. We upgraded to a 486DX running DOS 6 and Windows 3.1 later on and stuck with that for a long time, even skipping over Windows 95 completely.
When the original Pentium line was finally being discontinued, I decided to build myself the best pure-DOS PC possible for performance and compatibility with a Pentium 233MMX, Gravis Ultrasound PNP Pro, and I think a Matrox graphics card, for real non-emulated DOS gaming. I still have that computer, and it was quite inexpensive at the time. I plan to show it to my kids when they're a bit older.