There is no single right answer. I'll post several partial answers as time allows, since it is a long topic.
First, it depends upon what you want to shoot. For Jupiter, Saturn, and the upcoming Mars opposition, nothing beats either a webcam or an ordinary digital camera--no need for a fancy CCD, and film just doesn't cut it. The reasons: web cams and digital cameras can capture full-color pictures at a rate of several per minute (digital camera) or even several per second (webcam). The best ground-based pictures ever made of Jupiter are being made now by amateurs with these devices. By stacking dozens or even hundreds of them taken in rapid succession, one can increase the signal-to-noise ratio dramatically. Noise is reduced by the square root of the number of pictures (100 pictures = 10% of the noise left). Film just can't capture and stack so many pictures so quickly. Astronomical CCD cameras give monochrome pictures--excellent quality, but costly, and you have to insert colored filters and stack images to get color.