(UPDATE OCT. 20: The approach I describe article ended up being VERY interim. On Oct. 20 I found an even better solution: spotlight comments…)
This morning, as I’m sipping tea, it occurs to me that Mac OS X Tiger does allow me one possible solution to my document management dilemma: annotated pdfs.
Here’s what I’m thinking…
If I save my scanned documents as pdfs (rather than jpeg or tiffs), and open them in the Preview application of Tiger OS X, then I can use the annotate tool to add text notes. When I re-save the file, those notes become part of the original pdf, and the text in them is searchable.
Here’s an example of an annotated pdf I just created.
Then I can use the really fabulous desktop search tool built in to Tiger to search for specific text strings.
This, combined with the robust file naming convention I’m already using for these scans, will help me flag specific documents.
The trick is that pdf annotations created in this way appear as yellow sticky notes that cover parts of the document. So I need to be careful that my notes don’t cover any important information, like transaction details on a credit card bill.
This hacked combination of tools will accomplish most of what I wanted – although I still think a database might be better. However, so far I don’t need to attach comments or metadata to each and every scanned document. But I do need for my comments to be searchable and findable.
Now, the next problem is that most of my existing scanned documents are jpegs or tiffs. I’ll scan new documents as pdfs from here on out, but I may have to go back and convert at least some of the existing scans to pdf format. Not a big deal, though.
This will be good enough for now. However, I’d still like to hear about other solutions.
Gotta love Tiger!

Re: Notes covering up parts of the document, can this be toggled on/off as desired? I have never tried this feature with PDFs.
An interesting approach, but I’d be cautious about a solution that mixes the metadate (annotations) with the data itself (your PDFs) as if you discover a better approach down the line, you will have to re-create all the annotations.
If it were me, as a geek, I’d likely roll my own mySQL database, create some front end web formats for uploading/searching files and annotations, etc.
However, a readily built solution would be to create a new weblog that would be private (e..g put behind a password, make sure it is not indexed by Google). Each “post” could be your annotaions as the body of the post, and you can attach the files the same way you can do already in WordPress. You could create categories to “tag” them with as well. It’s already searchable, and this way you’d get free datestamping. You can get even finer levels of categorising using the Custom fields features of WordPress.
In fact, you do not even have to put it on a webserver; you can install mySQL on your Mac, and run WordPress as a local application. I do all my web development on my Powerbook and can run any system locally (blog, database, cgi) that runs on my webserver.
Weblog software is a reliable lightweight content management system, not just for diaries, eh?