>>s it possible that since I was VPNed to a server in Florida, Google "saw" my Outlook connections as if there were done from a different than my IP and from a different physical location?

This does happen to me when I'm traveling around the place, though more usually with Facebook than Google. It does look suspicious if you access from the East Coast and then moments later from Florida, so it's not a bad check by the providers. Re email, IME it usually does end up going via the VPN. Some of us do that on purpose to send outgoing email via a closed relay company email server. Unless somebody was able to sniff your VPN traffic you're probably fine, though VPN doesn't cover you past the router/machine you VPN into at the other end so if your email traverses their insecure wireless network on its way out, somebody might be able to sniff that. Not trying to state the obvious- but check to make sure you have ssl turned on in Outlook for gmail. Then maybe VPN in and google "what's my ip" to confirm the outgoing IP address from the customer.