I'm probably not typical, but I often have an ipsec connection up to one client or another, and I feel I have a "duty of care" - so the wireless router is attached to the "DMZ" side of the firewall, and I just VPN in if I need to access "inside" files from a wireless connection. If you care enough (if your situation isn't like mine you most probably don't) you can just put the wireless AP (and Squeezebox) on the DMZ side (you might have to port-forward port 5000 inbound for the squeezebox - acess from the server to the squeezebox is outbound and so should "just work" And there's SSH tunneling for the truly paranoid...
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