I've only "been digital" for about a year, since I bought my Pentax *ist DS digital SLR. I went Pentax because I had several Pentax lenses. Pentax is a fine company, but I don't claim it's any better than Canon, Nikon, or Olympus, the other three major DSLR manufacturers. It appears that two more, Sony (which acquired the technology of the now defunct Konica Minolta) and Samsung (which has a deal with Pentax) are about to become major players in that market. If you're interested in a DSLR, you won't go far wrong with any of those.
The frustrating thing about buying a digital camera at the moment is that the technology is changing so quickly. A friend of mine who owns the local camera store says the business has never undergone such rapid change as is taking place at the moment. My Pentax was the latest thing in budget-priced SLRs when I bought it a year ago; now it's no longer on the market. By the end of this month it will have been replaced by the Pentax K-100D, which has more features (including an anti-shake mechanism) and will cost about $200 less than the $900 I paid (including 18-55mm zoom lens). Logic and economics would suggest that this is a lousy time to buy a digital camera - but the things are such amazing pieces of equipment, and so much fun to use, that they're just about irresistable.
I'll take the liberty of offering one suggestion: in addition to the camera, allow room in your budget for a good image editing software program. The only one with which I have personal experience is Adobe Photoshop Elements, which I can highly recommend. It can be found for less than a hundred dollars. With a program like that you can start playing around with the world of the "digital darkroom," which opens up all sorts of new, fun opportunities.
Youth, talent, hard work, and enthusiasm are no match for old age and treachery.