Re: CS4 crashes when I send to print and pen tool loses the ability to keep the attributes of a multi-stroked line.

For the second, uncheck the New Art Has Basic Appearance in the Appearance panel flyout (small triangle, upper right). As for the other have you tried deleting and readding the printer to your printer list? Also, since nothing earlier than CS6 was tested with 10.9.x, the PDF method may be your only hope.