After six hours and one minute of trying to figure out a way to properly tag and browse his digital photos, Chester gives up and writes:
What I'm saying is that I think I'm going to fire up Adobe Illustrator to draw a scalable shoebox in which I will then dump all my gigabytes of photos.
I sort of agree. Any demanding, computer-savvy user will come to the same conclusion after doing a similar amount of research. It certainly can be done, but you have to have to be willing to sacrifice living for documenting. Speaking of that tradeoff, I'm on the edge of what I find to be acceptable, and I'm always working to find ways to either 1) not care about documenting stuff or 2) make my documenting workflow faster. Option #2 seems to be a fine solution so far, but at some point I think life will push me towards option #1.
And please don't tell me to use iPhoto. I've used it, and it's a piece of shit. If you're happy with a product like that, you're simply a different kind of user than I am -- and in fact, you are truly blessed. (The reasons for this blessing are all clearly organized in my head, but as a self-imposed push toward option #1, I'm going to end this entry now