Look, I'm going through the same thing you are - outboard or software - what's it going to be? And the answer is: I don't know. In the end, I got outboard gear (compressor, reverb) for the time being. But in the long run, I think software is the way to go, because with increasing bitdepth and sampling rates, digital's going to be able to sound as good as analog, I think. And soon, too - this stuff is changing almost daily.
About Cool Edit, though. Syntrillium's long overdue for a new version, to bring Cool Edit into line with other good editors, and that's going to cost me (and anyone who buys it now) the cost of an upgrade soon. Why don't you email them and ask them if you should buy now or hold off for the new version? They probably won't tell you (they keep their cards *real* close to their chests), but that way if a new version came out embarrassingly soon after you bought the present Version 1.2, you'd have a case for asking for a reduced price on the upgrade, I think.
