If you have an & in the author field, then this tells calibre that these are separate authors. Therefore entries 2 and 3 in your case will allow you to find the books using either author.
Your first example, however, illustrates an important point. As far as calibre is concerned it will treat two authors whose names are spelt differently as though they were two different people. This can apply to minor differences such as a different punctuation in their names. In your case it would consider "Doctor Sandra Cabot" and "Sandra Cabot MD" to be two different people which is probably not what you want.
That is the bad news. The good news is that Calibre makes it comparitively easy to correct such data discrepancies. If you use the Tag Browser and go to the Authors section then you can right-click any author and use the options that are given there to rename an author. Calibre will automatically apply that change to any books that reference that author.
Another point is that when you are editing a books metadata then Calibre provides aids to help you with keeping your data consistent. If you start typing an author name in then it will give you a list of currently matching possibilities so you can select from authors previously used. The other visual aid is that after entering an author the author-sort field is highlighted in red if the value there is different to what Calibre currently has for the author. This might be for a legitimate reason so it is only highlighted and not treated as an error.
I hope that helps - but if you were really asking a different question feel free to rephrase it.
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