i first played with a friend's 1MP Nikon Coolpix (late 90's?), but after trying it out, I decided that the features, ergonomics, and IQ were not yet good enough for me to get into digital. I waited to jump into digital.
My first digital was the Sony DSC-D770, a fixed lens, 1.5MP, slr-like digicam with optical viewfinder. The lens optics and ergonomics were superb. Focus was slow, and focus accuracy was a problem with that camera.
My next jump up was when the Nikon D100 came out. I HAD to have one, I bought one new for $2000 for the body alone (around year 2002-2003), and I still have it today. I still use it with my large array of Nikon lenses when I'm feeling nostalgic.
I stayed with the D100 until March 2010 when I jumped into the micro 4/3 format. Of course, I still shoot film but micro 4/3 is currently my digital format choice.
--Warren