As a beginner I've learned that "obasan" means "aunt" and from watching Japanese movies I've also learned that it can be used to address a woman with a meaning something like "lady" or "madam".
There is a kind of set joke that crops up in a small number of the anime I've seen that involves a small child addressing one of the female leads as "obasan" to the evident annoyance of said female lead. Since the female lead is usually in the 18 - 25 age range, I'm guessing that obasan implies either an age considerably greater than 25 or, possibly, some kind of frumpy-ness or staidness. It certainly seems to imply something that an 18-25 year old female doesn't like to have applied to them.
So what are the connotations of "obasan"?