I have a question, I want to know if I could go out and buy a USB to serial (With the 9 pin plug) and put my PC to Mac serial cable in there and transfer stuff from my PowerBook 150 to the iMac.

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Quite sure that you can't. The Basilisk II (Mac emulator) documentation says, if my memory serves me, that even though it's possibly to use the serial ports from within it (and I've connected to my Newton with it) it is "physically impossible" to connect an emulated Mac to a LocalTalk network. I'm not sure what part of the chain makes it impossible, but I think it's something about the differences between Mac serial ports and PC serial ports. Not sure, though.