I hope organisation doesn't dropout on idea of giving students project on this idea, cause I have been working on it for a while, I also had introduced myself to the community in this forum- students interested on GSoC and also specified that I wanted to work on this particular topic. Lately seeing this thread, I am realising not many are impressed to have this idea as a 'GSoC project'. But I think there is more to it.
As specified by @zopyx anchors can be generated by unique IDs rather than headings, but we can also follow approach given in original Idea list provided on Plone's site itself (see suffixing the anchors with number in case of duplication).
Positioning of editing bar is one straight forward concern. If it may seem, this work wont require that much time, I shall be more than happy to take inputs from community and try more creative stuff to enhance user interface, which I have also specified in my proposal that I shall be submitting soon, of course before the deadline.
That is why I chose to work on project called 'Editor Improvement' and not 'Auto-generating anchors for heading and fixing the editing bar position'.
I hope my efforts dont go in vain.