My question is why do you need to print from Classic? If it works when you are in OS 9 natively... and it works when you are in OS X, then why is it that you need to be in Classic to print? It would seem, at least to me anyway, that there would be little need for you to be able to print from Classic.
After all, Classic is merely an emulator. It really wasn't intended to be used for complex or involved uses. Sure printing isn't a complex thing, but Classic's only real viable use is to run some older applications. When it comes to using external peripherals and networking, Classic has always fallen short. The simple answer is, that certain features and hardware simply won't work in Classic, no matter how hard we may try.
Since you seem to have the ability to boot into OS 9, I would suggest doing that when and if the need calls for an OS 9 application.