I'm coming a bit late to this discussion, but I've been through the same exhausting process in the last few months. Usual story. I fall into the keen amateur shooter category. Always organised my pics neatly in folders. Very logical. Could find things quickly.
Until now. Just too many pics. Needle in a haystack.
I think one difference between film and digital photography is that the "keen amateur" has software needs (particularly cataloging needs) very similar to the pros. Pixels are free. We shoot more often. We all shoot hundreds of pics at an event without a second thought. Even casual and occasional shooters will eventually end up with thousands or tens of thousands of pics, and they won't have a clue how to find the ones they want.
So it's worth looking at what the pros do. The DAM Book by Peter Krogh (http://www.thedambook.com/
) is a good starting point - a thorough look at the theory and practice of digital asset managment. For what it's worth, he uses iView, Bridge and Photoshop.
If you're not sure you need to go that far, it's still worth taking a look a Peter Krogh's forums (http://thedambook.com/smf/index.php
), where they discuss this stuff in great detail. Very helpful.
In the end, I plumped for iView. Nice GUI, fairly intuitive, nice and quick to use once catalogs are built, and a lot of pro photographers have been relying on it for some time, which must mean it's reliable and scalable. It should cater for all my needs for the foreseeable future. As MrCrispy points out on the first page of this thread, MS bought iView and is rolling it out soon as v1 of MS Expression Media. As MrCrispy also points out, views will vary on whether this is a bad or good thing.
On the plus side, registered users of v3 of iView Media Pro will get a free upgrade to Expression Media v1.