We still don't really know what's wrong with the pictures from his digital efforts. He just says the analogs look better.

Look better how? Color, exposure, contrast, noise, flash exposure? Many many factors.

That said, I recall being quite disappointed with the results of my first digital SLR, until I realized, as Franglais said, it's up to me to make it what I need it to be, and possibly fix the camera settings to approach what I like to get out of it. My first digital was a Sony point-and-shoot which I was very impressed with. I much preferred it to my D50 until I "learned" what needed doing with the D50.

It didn't help that the D50 was used, and I inherited some locked-in settings that were entirely inappropriate to my shooting, that took me quite a while to find and fix.

The other thing that occurs to me to wonder about is whether we are judging the pictures by how they look on screen, or how they look after printing on an inkjet. (I truly hope we're not talking about color laser printing. A color laser printer is completely inappropriate for photographs.)

Getting printed output to even approach what you see on the camera screen or the PC screen can be incredibly difficult. I've tried repeatedly to build a color calibration for my printer, but I've pretty much learned that the best results come by cranking up the brighness on an image until it's almost unviewably on the screen, and miraculously enough it prints incredibly nicely!