Hello!
I am an OS X system and UI developer.
I have experience creating printer drivers - specifically, one of my long term projects was a CUPS module (including non-trivial USB communication agent, CUPS filter, custom CUPS backend that rerouted the printed stream into the USB agent, CUPS UI extension pane). Besides actually printing, it supported uploading documents onto the cloud storage, downloading them whenever the device is connected, etc.
Can you give some more details about the printer device you have?
I suppose you already have a working windows driver?
Do you also have the device specification?