At the 9.1 release of ArcInfo, the functionality of Maplex for ArcGIS was added. If you have an earlier version, or you're licensed for ArcEditor or ArcView, not ArcInfo, then you need to purchase Maplex for ArcGIS to gain these labeling functions.
By placing more labels properly the first time (automatically), you will save the time and expense of editing overlapping labels, adding missing labels, and repositioning labels.
Absolutely. Maplex for ArcGIS provides many options for placing complex text and labels inside polygons. Maplex allows you to make the parcel maps that you need without having an operator create separate annotation strings for each parcel. By saving annotation to the database as feature-linked annotation, you only have to create labels once.