I've no idea why Word isn't responding. (Simply restarting your computer might fix the problem).
OCR programs can generally only 'read' clear typescript. Technology is available which can read some forms of handwriting. (I believe that Post Office sorting centres have machines which can read some hand-written post codes). However, it requires a great deal of computing power and the necessary software usually costs mega-bucks. (When your brain interprets those three squiggles on a page as the numbers 1, 2 and 3 it's using a lot of computing power, together with a mental 'program' which has been gradually refined through many years of use).
OCR technology is still really in its infancy. The software available for home PCs is still only barely adequate for reading clear, type-written text in a non-serif font and with a good contrast ratio between the text and the background. I rarely use it, simply because I find that I can re-type the original document in about the same time as it takes to scan it and then correct all of the errors introduced by the OCR program.
Try using the OCR program to 'read' a well-spaced, clearly-printed page from a book. That will illustrate the limits of the technology. (There might be some fairly expensive commercial programs which can do a better job than the free one, but none of them are perfect).
For background information, see here:
http://en.wikipedia.org/wiki/Optical_character _recognition
Chris