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Will the Mac see my Windows shares natively, or will I have to install Samba? The last time I installed Samba (4-5 years ago), it was a pain to get it working.

It's built in now. Just go to the Network page and you should be able to browse the network and select your Windows machine. You can do it the other way around if you want and mount the Mac HD from your Windows machine by enabling Windows Sharing.