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Commodore 64 and an ImageWriter II printer...

Does the ImageWriter have a Centronics interface, or RS-232? In any case, you'd need some special interface on the C64 to make it work. There were several Centronics interfaces, some with print buffers and other goodies. Once there, I suppose a wide range of printers can be supported.
 
Should be fine. You will need an RS-232 interface on the commodore end, then use an apple 25pin to mini-Din cable.
 
Unless you're writing your own software or the software has conversion built in, you'll probably have trouble with PETSCII (CBM's different character set). Commercial printer interfaces (and drivers that used the user port) usually had conversion built in, but most (if not all) of those were for parallel (Centronics-compatible) printers.
 
Any printer that is compatible with the old Epson matrix printer(s) is likely to work with most software, without special drivers.
 
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