I have used DeedMapper for several projects, and have found it to be very 
useful.  It accepts a variety of means of designating angles and distances,
including some measurement systems that are pretty obscure, and allows for
custom definition of measurement units, meander lines, and provides area
measurements.  The user inputs data from the document, the program plots
the lot, and you can then drag-and-drop it wherever in your diagram you
want to put it.  You can print plots and/or text.  It is most useful when 
researching multiple properties, properties with complex boundaries, and
lots that may bear no resemblance to present day tax assessors' maps.
 
Drawbacks are that it doesn't allow more than one meander line in a single
document, and it will not calculate missing distances on the basis of area
measures.  This sometimes requires trial and error work with missing
measurements.  Also, it does not allow copying of metes and bounds from one
document to another; they must be entered from scratch.  Scale of plots is
adjustable, but not to a large enough scale to make sense for urban
projects.
 
Overall I've found it useful and cheap (about $100).  A windows version is
out, but you'll have to check with Direct Line Software to see if it's
available for Macintosh.
 
Lauren J. Cook