<p>The text box has a 2000 char limit. If I upload a word document, should I still stick to the char limit?</p>
<p>I don't think you have to. Try uploading your document, then use print preview to see if it's all there. I think that the 2000-character limit <em>may</em> indicate that they don't want a terribly long essay, though. But that's speculation.</p>
<p>The instructions state that if you want to upload an essay, that would be fine. Max. number of words isn't mentioned. If they wanted you to stick to 2000 characters, I don't think the upload option would have been included. Stanford for example, makes you stick to character limit in the short supplemental essays since writing over that limit won't work in their boxes.
So I think writing a reasonable number of words would be fine as long as it's not more than a page, which seems to be the standard acceptable length. My D wrote a 550 word essay, her friends did around the same.
Harvard is pretty flexible and open about allowing for anything that you feel will show yourself. For example, my D called them about a supplemental research stuff she wanted to send, and they were quite open to having her send what she wanted as long as it was within reasonble limits.</p>