Just some ideas...
Making a hand printing press is relatively easy, there's some details here
http://chestofbooks.com/crafts/popul...teur-s-Ne.html
You have to scroll down past the adds. Keep in mind that even this one is probably more sophisticated than strictly necessary. You could easily create the type set and lay the paper onto it and then simply lay weights on the whole lot to ensure the paper gets printed on (anybody remember doing this sort of thing in early childhood at school, I remember carving shapes into potatoes and using paint to print the shapes onto the paper)
The webpage also briefly mentions making lead pencils which will probably be the only way to ensure some sort of writing implement when the pens run out.
Rather than overprinting whatever paper money is still available it might just be easier to pulp whatever scrap paper can be found and produce sheets of what is basically recycled paper then use the hand printing press to produce the scrip that's needed.
Otherwise you might end up with 5000 $10 notes and only 100 $50 notes if that's all you could recover (with paper money worth less than the paper it's printed on, it may very well get used to light fires or even wipe backsides so there might not be much of it around).
The print type could be hand carved wooden blocks or metal type that has been recovered from a printers. For images it's probably easier to carve the image onto a wooden block (anyone with even basic carpentry skills can carve out an image if someone has drawn it onto the block).
Alternately, images and large bodies of text could be done by the lithograph technique
Some info here
http://en.wikipedia.org/wiki/Woodblock_printing
http://en.wikipedia.org/wiki/Printing_Press
http://en.wikipedia.org/wiki/Lithography