1.) It appears that a user must type an exact match to get a search result. I was hoping for a wild card search.
Edit your userlist, scroll to the bottom, and ensure its mode is set to simple any instead of simple is.
2.) I created for search fields (Name, City, State, Zip) but only Name comes up in the search box.
Ensure your new fields are set to be searchable. Once done add them to your userlist in either of the 4 columns (column needs to be enabled) or edit your userlist and set it to display all searchable fields.