[Powerhouse]

1) My media is stored in two locations: A NAS server in the basement, and two hard drives on my existing HTPC, which will be moved to a different room for a second TV. I'm guessing that adding a NAS share will be easy enough since it's NFS, but how can I add paths to the Windows based NTFS-formatted drive(s) across the LAN? The internal 500 GB HDD won't be nearly enough storage space for my media (I'm around 6 TB between all my devices).

Just add them as a SMB share.

I'm not sure what that means. As I said, this is all new to me, and very much dark magic. Do you mean just share the folder from within the Windows 7 box and the Shield will find it? What about permissions--anything specific I have to set up?

Also, is it possible to run a VPN with the Shield? I'm not comfortable doing anything without a VPN if at all possible.

I run a VPN (TorGuard) without any issues, you just have to make sure that the VPN you choose has an Android version available.