> One big TIFF is an insane way to package icons for the web.
Not really. You almost always would need to resize or somewhat edit them anyway. And if you care about performance, you would want them in a sprite sheet, so you need to recombine them.
Having them in a single document is much more convenient than having a few hundred open documents in photoshop.
That is relevant for the web. Really though, I think fonts are the way to go for web icons. Crisp at any resolution and CSS style-able. Bitmap icons feel a bit 2008.
One big TIFF is an insane way to package icons for the web. Also why use TIFF over PNG?