Started with my first camera at around 15 with a cheap camera that my dad picked up for me. It was expensive for film so I stopped shooting after that, especially after getting a bunch of blurry shots of fish.
Fast forward to college w/my reef tank and my roommate, who owned a Sony Mavica at the time. I can't remember how many megapixel(s) it was. Looking back at it, it was rather dated, using floppy discs, which held about 20 shots. After that, you had to dump the images or insert a new floppy. It was time consuming, but that camera actually had decent AF and some of the shots didn't come out bad at all (way better than anything that I was able to produce before then).
My next encounter wasn't until a few years back with the introduction of the Nikon D70. I sat on the fence for a few months until it fell below the $1k mark (after rebates) and snagged it up afterwards. I burned through 25k actuations the first year and attended every group outing that I could make. I also went through lens acquisition syndrome and picked up everything that I could afford.
During that first year, I shot my first wedding and some other paid jobs which paid off the camera. As I picked up more event photography work and shot more, I was slowly growing out of my D70. Luckily Nikon introduced a Nikon D200 somewhere along the line and I had my sights locked on it. I quickly sold off the D70 to fund part of the D200 (actually sold the D70 to the couple who I shot the first wedding for
) and picked one up from their second batch (first batch had some issues). The D200 was a vast improvement over the D70, but I needed a second camera for backup and started looking around.
Three months after acquiring the D200, I met a Nikon pro that was retiring and was parting with his gear. Amongst the list of items was a gently used D2X with around 11k actuations and he made me a deal that I couldn't refuse at the time. I've been shooting steadily since then with the D2X and the D200 as my backup.
Along the lines, I've had the pleasure of shooting with other cameras since my bro shoots with Canon gear. He owns both the 20D and a 1DMIIN (great camera) so I dabbled with some of his equipment.