As far as when to submit sitemaps, you do not "need" to even submit one. After your initial sitemap is submitted, as long as you have a strong interlinking structure in place, your new pages should be crawled. Submitting a sitemap when you add new pages is more or less a "heads-up" to Google saying, "I added new pages here... you should crawl them when you have time."
Now, if you remove pages from your site, you should also make sure that your sitemap reflects these changes. If you do not, you will start to get 404 errors in Google Webmaster Tools.
I don't think you can overdo it; however, you would probably make less work for yourself if you only resubmitted when you are 100% sure you actually need to.
Does that make sense?
Mike