My very first digital image was in around 1986, I was teaching photography at a local college and they had an early digital camera. I found it fascinating, but wasn't tempted because of the image quality.
The first one that I bought was in 2000, pretty sure that it was an Olympus. It was a cracking camera for its time, but had a small sensor so limited in terms of image quality. It ran on 4x AA batteries and I only got about 20 shots per set of batteries.
What modern photographers may not realise is that costs of both cameras and storage were very high back then. This camera cost me £1500 (the competition was the 3mp Canon 30D (?) which cost £2000, body only, and the memory cards cost about £1 per mb . . . I bought a single 128mb card for £125.
The image quality was probably about on par with 35mm film, so very limited in terms of professional use but I remember my first big shoot with it, basically a fashion-type shoot for a workwear manufacturer and they were delighted with the results.
The shoot went well but was slow, because the memory card could only hold 9 shots, so each product ended up with just 9 shots, then we had to stop for coffee while I uploaded the shots to my computer. My assistant told me that he knew another photographer who had a microdrive, basically a non solid-state drive card that had 340 mb and that cost £340 - should he give him a ring and see if we could borrow it? We didn't get it, apparently the other guy had hoped to get the shoot and he wasn't happy . . .
My next digital camera was a Fuji S2Pro, at about the same cost, the image quality was much better but the camera was a bit of a nightmare to use, and very slow. I then bought the next model, the Fuji S3 Pro, which was a big improvement. Next up was the Kodak 14N, full frame and superb image quality at 80 ISO, but any shots taken at 400 ISO were terrible. This camera created very sharp images, mainly because it didn't have an anti-alias filter, but because of the terrible flare problems it could really only be used in the studio. I paid £5000 for it and then, a month out of warranty, the sensor failed and Kodak wanted £4000 for the repair, so I bought a Fuji S5 Pro. I then bought a Nikon D700 and a Nikon D3 and still use both of those. I still have most of my old digital cameras, they're in a box somewhere.
Those were the days, and I found that digital photography encouraged much more experimentation, but modern technology is so much better, cheaper and easier.