I'm having pretty much the same problem...
Printing from OS 10.3 to a HP Designjet 500 using Vworks 10.5.1
Every now & then - a drawing just won't print... sometimes crashes Vworks. Allthough you can then restart Vworks & print a different drawing just fine...? As Aidlin says - once a file has had this problem it won't print from that machine - ever !
Have remade the printer Q & re-installed printer drivers & Vworks.
Have checked the print centre when trying to print & the job never appears - no error message - nothing...
This is driving me mad & costing me a lot of time & money - please help !