Hi Dan,
It sounds like you have been discussing label printers with Philp at Microsoft.
With regard to connections by Azure joined machines, would a local printer on the Azure client system be okay?
You can use the LPD service in the server, either Windows or 3rd party, and add a local printer, with the correct driver, with the printer set up to a Standard TCP/IP port in LPR mode.
LPR Byte Counting must be enabled
For the Windows shared printer, set up the share using one word. NO spaces please. You can get the port working but keep it simple for the share name.
Thanks