What a cool read!
I've only really begun to take photography more seriously over the last four years or so. That said, the first camera that made any kind of impression on me was a Samsung AF Slim Zoom my parents bought for me to take to the World Jamboree in Holland in 1995. Although it was a basic P&S, it did have a decent zoom and also had a bulb mode, which I used to mess around with quite a bit. It was good to travel with, and if I had to get another P&S film camera, I'd probably get something similar. It was stolen by a former friend when I was in University, and I was cameraless for about eight months.
I bought a used Rebel G with a kit lens and a 420EX, and started to learn what SLRs are about. I also bought a used 100-300 EF zoom to use as well. That setup lasted me until November 2006 when the camera crapped out on me at a motorsport event. It also somewhere along the line developed a hole in the case, just below the shutter button. I'm pretty gentle with stuff and certainly wasn't using it to build a deck, so who knows!
After getting frustrated by the lack of reliability and durability of the Rebel, I went into a local shop and eyed up a Canon Elan II used. It was over 350 CAD and that seemed a good chunk to save towards digital. Then, one week before Christmas I went back in and it was under $200 including a grip (with batteries that have lasted a year! ). It's been fun to shoot with, and Ive enjoyed the added level of control.
Finally, this last month, I have moved to digital with a 10D and a couple of new full frame lenses. It's been great to learn more with, especially trying newer creative things. I've never had gobs of money to spend on photography, so eliminating the cost of film has been nice.
That said, I really do enjoy something about film, and can't wait to get some time out shooting with the new 17-35 on the Elan!
Over the last year, I have come into possesion of all of my families cameras. I've got a few brownies, as well as some bellows cameras (not 4X5, 120 film I think) dating as far back as 1913. I am hoping over the next year to start seeing if any of them are functional enough to shoot with. I'm also eyeing my dads Zeiss Ikon, and my girlfriend has a Mamiya RB67 which I'd like to try sometime.