My Choices for Leaving Windows 7 for Linux

Hello. I want to discuss my choices for leaving the Windows 7 OS.

I hate Windows. I want to go to Ubuntu Studio. But in my SOHO my business partner has 20 years of Windows Word files for legal cases. He is computer illiterate. So I send his emails. Anyway my choices as I see it:
[1.] dual boot Windows 8.1 [I have a legal copy] and Ubuntu Studio
[2.] Run Ubuntu Studio and run Windows 8.1 in a VM.
[3.] as a last resort run Windows 8.1 only. I do not want to do this!

I could go into pros and cons for thats the TLDR for now. Ideas? Thank you.