Do your company policies and the practicalities of your software let you put enough of your personal stuff on the work laptop for the duration of the trip, and remove it afterward? Granted, it's Windows and not Mac, but iTunes is also available for Windows, most other Mac software has an approximate Windows equivalent, and you obviously know how to use it.

Or, could you run Windows emulation on your Mac and take enough of your work stuff? (Depending on who you meet with on the road, this might look wrong.)

That said, lots of people carry two laptops. You won't have a problem with security. Whether or not it's worth it is totally personal.