Move MultiBit from Mac to Windows
What I would like to know is if all of this data can be transferred onto a Windows environment with minimal fuss.


Yep. Find the data directory on the Mac. Copy out multibit.wallet. Install MultiBit on Windows. Find the data directory on the Windows computer. Copy it there.


  He also says he has a "bridge" into his "trezor" that he needs as well.


He's probably talking about the Trezor plugin. This page explains how to set that up in the first paragraph.