My user has a couple hundred Contacts representing basically three groups.
Each group is sub-divided into smaller groups, then smaller groups, etc.
down about five levels.  The user is using a multitude of categories to do
this but it finding this very cumbersome.

She reports that to use one category for the To: in an email works fine.
However, if she wants to use another category to CC: she has to start a 2nd
email, get those addresses, then copy/paste into the original email.

She does not want to create separate Distribution Lists because there are
too many overlaps to easily maintain the lists.

Lastly she wants to know if it is possible for the average user to add a
custom field into the Contact records.  Does anyone have any ideas on any of
the above issues?