I like this idea a lot however how would it work with pages generated using a CMS? If someone adds sections to a page does the skitpto automatically know how to adjust? Or is there a feature built into the programming to allow the CMS editor to simultaneously adjust the skipto links to the new areas that were added?

The SkipTo tool looks for headings in the text and exposes them. Aside from adding the JavaScript to the HTML, no further work should be need. As long as the content is properly structured HTML, then the navigation should be displayed. New content would automatically have the headings added, because it's just some JavaScript applied to the page.

We might want to adjust the SkipTo to restrict the links to just the content within the body of the page, but that should be easy enough to do. 

It makes the invisible (heading structure) visible and displays it much like a table of contents would.

I'd say my only other issue might be with added javascript on the page it might slow the site down. But this may not be the case, teams would just have to test and see in their own environments.

It is definitely worth testing to see what the performance impacts might be on both mobile/desktop and new/old devices. JavaScript isn't free after all. It does have an impact on the users.