Hi Tom,
I am by no means a Word OLE guru, but I do have a thought on this

if filecnt > 0
for n = 1 to filecnt
WITH oword
.Documents.Open(print_file)
.ActiveDocument.PrintOut(0,0,range,"",from,to)
.Quit
ENDWITH
delete file (print_file)
endfor
endif

I believe the problem is in the 6th line of code there '.Quit'
This closes the Word application and thusly, there is no way to open a document. I believe all you wanted to do was close that initial document, and instead you're quitting the entire word document. Try just using this

.ActiveWindow.Close

Hope this works for you.