Can anyone make me feel like a winner? spam@adamnorman.com —it'll get there.

Evernote (Evernote.com) might be too small for your needs, and it's not open source, but it: - Has OCR - Is very cheap ($6 a month for the pro version, free for the light version) - Recognizes handwriting - Accepts tags - Has a web interface (and a desktop client) Its only limitation is the 500 MB monthy upload cap. Since you have hundreds of files to get through, you will go over the cap if you upload all at once. But since scanning those things is going to take you ages, you might be fine. Also, if your boss is still collecting paper, he's probably pretty old-school. Evernote is dead simple to use.

Wireless Nomad is still doing just fine. I'm writing over their lines.

What if they don't want to turn a profit? Isn't that worth talking about? And, FWIW, they do make enough to cover their costs. Check their FAQ.