Every time you rewrite the web page, you should give it a fresh meta title and description. We rewrite our web pages every few months. Our latest batch will include over 35 pages, all original and rewritten from our current pages, with new metas for each one.
Rewriting content from static to fresh and original never hurts - I don't think you can ever do it too frequently to get penalized. However, a better way to use your time and investment than rewriting content daily (which wouldn't be as effective) is focusing on producing new content in the form of blogs, guest blogs, whitepapers, etc.