Scanning and scanning

I've restarted a project I began about a year ago, scanning all my paper-only game writings into digital form. Some of the paper I have in files is 30 years old. That means it's A) falling apart, B) fading with age and C) really interesting to read (though probably only to me).

Strange things you discover when looking at old campaign material:

• Naming conventions change over time. Everything from Latin-like to unpronounceable to common is fair game.
• A city with a standing army of 169,000
• Every inn and tavern is still run by the thieves guild.
• A single page in the back of the city map key with the word 'NINJA' on it. Must have been important.
• 75 pages of computer generated text blocks detailing sunrise, sunset and the phases and rising and settings times of three separate moons. High and low tides too.
• 400 pages of 2nd edition D&D NPCs, complete with stats.
• The number of magic items found in a single tavern's list of NPCs is staggering.
• A garden plan for a house I owned in 1988. Uh... what?
  

Initially I was going to integrate this all into a wiki so I could reference and link it all together in a way that made sense. I've given up that idea, mostly because half of this stuff isn't connected and doesn't makes sense. Instead I'm just scanning everything to digital format, disposing of some of the really unreadable stuff, and reorganizing the rest into more compact and organized notebooks.

I'm using a flatbed scanner to digitize everything into 150 DPI jpegs. I'm applying a broad naming scheme to the files (right now I'm on Bestiary070.jpg). Once I have this all captured I'll try to figure out what to do with it. Some of it is fit only for filing away for nostalgia. Some of it I may transcribe to an editable digital format. I'd like to OCR it, but I suspect my handwriting will prevent that.

Has anyone else undertaken a project like this? Any suggestions on organizing a bunch of document scans into coherence? Any recommedations for Windows-based (free) OCR software?