A few questions... How much you willing to spend, how many details you need to catalog, what applications do you already have?

Many graphic applications like Photoshop have built-in "catalog' systems where you can add anything from brief descriptions to more detailed notes and generate thumbnails. I count my collection of stills and captures from vids not in the thousands, but the hundreds of thousands. iMatch, ACDSee, several other free standing applications fall into this category and most are well under a $100. An advantage is they are fairly automatic. In other words they will generate the thumbails on their own and you can sort them various ways. The downside is most don't allow you many parameters to "search"

If you have an extened collection and need to search for specific things about the image you're looking for, a database type application capable of searching similar to Goggle where you just enter specifics and a bunch of hits come back are idea, but take a very long time to set up and then you must force yourself to get into the habit of filling out whatever fields you set up and do it religiously or its next to useless.

I use both types. I've mentioned it before and will again. A easy to use and highly customizeable database designed for video collections is CATVids.

http://www.fnprg.com/catvids/catvids.html

This is a true database. The advantage is it starts off with about a 100 fields already to go and you can customize from there adding, changing or deleting fields you have no use for or have to have plus it generates dozens of different type reports on top of the "pages" you can just click through. I am constantly using the Vegas capture a sill features (floppy icon above preview window) or saving from Photoshop whatever image I need, which gets added to the database. Then I can easily sort on a whole bunch of fields. Country, date, project, location, talent, etc., and then in seconds get a report of everything that matches that's in my database. So for example I may only remember blond, red thong, Monaco, and in seconds I'll get a list of those photos and where I put them. A down side of course is setting such a database up It takes a great deal of time initially. The other thing I like is it has a comment field so if I need to, some thumbnails can have comments as long as this post.

If that's more than you need to lessor applications, not real databases can ususlly keep track of multiple lists. Like with ACDSee I have maybe 300 or so folders set up. You another way is simply set up various folders from Windows Explorer, give them appropriate names, then get more crude sorts that way. Again, it depends on how big your collection is. If you only set up a folder and put all your sunsets in it and you have several thousand sunsets, it still will take sometime to sort through to fine the ones you want. So if you have a really large collection you either will be investing lots of time to set up some database type or spend lots of time every time you seach if you use the cruder methods of just setting up a bunch of folder in Exploer.

I've tried several different pieces of SW as well. As has been posted, it depends on "how" you wish to retrieve your photos. I also think it depends to a certain extent, on how your mind sorts and processes info.

Here's what I've done, but i like things organized (somewhat) chronologically, since I do this almost exclusively for family reasons, and don't necessarily need to retrieve a bunch of "sunset" shots, for example:

First, decide how to catalog the images. I set up a "Pictures" directory on an external HDD. Next directory level is each year (2005, 2004, 2003, etc)
Next directory level is YearMonthSubject. Thh photos go on this directory.
It looks like this (for example): Pictures/2004/2004JuneMexicoVacation

You can then use a file catalog program (as described above) to further tag each photo or group of photos or directory (sunsets, family, flowers, or whatever).
A good one I'm getting started with (and it's free) is Picasa2, available from Google here: http://www.picasa.com/
iMatch looks like a good one as well
PainshopPhotAlbum looks pretty good as well (I have not tried it)

You're going to have to try several (if trials are a available), and spend a LOT of time organizing them (unless they already are, of course). If they are not organized to begin with, it'll be a frustrating experience, and the software can ease the pain.

Here's my recent experience:
I just went through this with my mp3 collection this weekend. I've been ripping and cataloging select cd's for several years to my desktop PC (Have about 2500 mp3's so far). I Finally got an mp3 player last week (40 GB Creative Zen Touch - nice player) and started transferring music to player. THEN I found out that most of these players use the id3 "title" tag to catalog the songs by, NOT the filename (silly me!) . While I was mostly consistent in namging the files over the years, I was NOT consistent in tagging them with the id3 tags. Hence when I looked at the files I had transferred, I had a bunch which were named (In the "title" tag, that is) Track 1, Track2, unknown, etc. ARGGGGHHH - time to start over. I found a little piece of freeware which I could use to retag, and if necessary rename the files, either individually, or in batch mode. It took most of the weekend (late at night, since days were spent with my family skiing and celebrating Easter), but it's done now, and I can sort and find any song on the mp3 player based on title, artist, album, genre, etc.

Sorry about the long post, but It is relevant, since I'm going to be doing this with my photos as well. The Picasa SW mentioned earlier in this post seems to be able to suit my purposes - you may want to give it a try.

Phil