First Pentax: Optio 430RS. Truly dreadful - I think it was made by Casio, who had an identical camera with a different model name.
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First film SLR: Canon AE-1
First Pentax DSLR: *istD (stupid name that nobody knew how to pronounce)
First camera ever (which shows how old I am): Kodak Brownie 127 just like this one:
In a way I envy how you have been able to see a whole span of the evolution of photography from early brownie to dslr.
I feel that learning curve was harder then due to the cost of film/development (shoot more, pay more), harder to reference to shooting settings unless one wrote it down and no chimping

More emphasis on getting the shot that 'bokeh', shallow DOF and all that (mostly reserved for pros who could afford to burn film)
In the past, I was usually concerned with exposure being enough and shutter speed being generally hand holdable with whatever film I had in the camera (usually ISO100; ISO200)
Nowadays, there's DRI, highlight/shadow recovery in PP; etc.
Certainly very different now.
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