Think of it as 'chief' as in most important or highest rank then it works for main menu and boss.
I think so. In fact, I would say it is a better translation. According to PMEG, estro has more to do with the commanding rank, and ĉefo with the hierarchy (not always related to the capacity to give orders, like in an academy where the most senior professor is distinguished in some way).
It may be a bit confusing, though, and I suppose both are valid in most situations. But, for instance, if you are talking about the president of a republic like Italy, where his powers are very limited, I guess you should call him ĉefo, while the prime minister would be more of an estro to the ministers in the cabinet.