I agree that the digital scanners cost far too much right now. For me, it is not worth the extra cost where I live as not many services besides the state PD (which is hinting at encrypting anyways) and the boring yuppietown to the south of me are digital. Hardly anyone is even trunked for 40 miles around me, and this is Central CT. A very densly populated, and RF-intense region.
Even on the used market, the Pro-96 and the 396 fetch a high price. The reason is that supply is currently meeting demand. And no one is having trouble selling $400-$600 digital scanners. The only digital scanner that no one really wants much right now is the 250D, and those sell very cheaply on ebay and other classifides.
Once a new generation of digital scanners come out, you will see a quick drop in the Pro-96 and BC 396 prices out there. You already can see some of that as many Pro 96 and 396 owners trade up for the GRE 500.
Also, the added complexity of these early digital scanners have removed some of the "fun" out of just being able to open the box, mash some buttons, and start hearing things. Its not that you HAVE to have a computer to program the things. I think everyone has one ( or 12) by now. But not being able to do much of anything until you figure out the computer program kind of flys in the face of how scanner enthusiests enjoy their toys. (turning knobs, and mashing buttons in a more
analog way.)
Wait until a second (or maybe it is a third gen now) digital scanner is released. You will get one of the current ones cheap, but the improvments will probably be so great that you will just want to buy the new one anyways