I switched from Legacy 7 to Reunion when I switched to an iMac. Reunion is written for Mac by a Mac user, it is highly rated as a program and from what I read it compares favourably with Legacy, FTTM & others.
As for doing what you ask I am not sure as I am not all that familiar with it at this time, as I do most of my history work on Ancestry.com.
I had no problems with gedcomming all my info from Legacy to Reunion. Being built for the mac means it runs seemlessly with everything else.
I suggest you look at the website and check it out. It is rated as the top genealogy program for macs at this time, followed closely by mac family tree.
To go virtual and install Legacy on your mac, easy using mac "Boot Camp"but means you have to obtain and install a Windows OS, along with all the security stuff that goes with having a windows system. Lots do it but one of my reasons for switching to mac was to get away from all that.
Check them out at Reunion. One thing seems certain in that no program will give you everything as they do things differently so it comes down to what you can live with.
Hope this helps.