Billy,
Both cases are differences between AutoCAD's definition of a polygon vs the shapefile format and in both cases your intuition is correct.
The library doesn't have much in the way of corrections because geometries are stored as lists and python list manipulation is so simple.
So in the case of closing the polygons, just duplicate the first point as the last point if they aren't identical already.
In the case of the negative area, counter-clockwise points are used to create holes in polygons (doughnuts) according to the shapefile spec.
There is a function in the library called "signed_area()" that takes a list of points and returns an integer. If that integer is >= 0 then the points are counter-clockwise and you need to reverse the list to get a positive area. That way you don't have to do the check in AutoCAD.
Let me know how that works out for you. Thanks for the feedback.
--
Joel Lawhead, PMP
E-mail: jlaw...@geospatialpython.comWeb: GeospatialPython.com
Twitter: @SpatialPython