I prefer outlook as it works so well with Windows 8, mail, skydrive and Windows Phone. Also Gmail doesn't allow exe files even when zipped, you can send those but not receive.
About the scanning, I created a fake email on hushmail from public computer couple of years ago. Then sent an email in there from my hotmail saying something like "continue with the attack on the white house. Allah akbah" but got nothing, not even a single drone strike xD. I might be on some list though if I ever wan't to spend holidays in US.