WiFi attacks are not necessarily passive, ARP poisoning can redirect a victim's traffic to your machine at which point you can MITM to your hearts content. If you have trained your users to ignore the inevitable security warning (Grandma isn't going to check an SSL fingerprint) they are going to be operating under the false assumption that their communications are secure. For most people this is a worse scenario than the NSA having their data.
If you are talking about a thick client, with the appropriate checks built in, I'll agree that it's possibly more secure. Other than that, its only possibly more secure if you are the only user or you can eliminate the security warning (e.g. by distributing the certificate).
I'm skeptical that any US based company could get away with not rolling in the face of a subpoena/NSL so the protection provided by the service provider knowing they have been compromised is minimal IMO.
If you are talking about a thick client, with the appropriate checks built in, I'll agree that it's possibly more secure. Other than that, its only possibly more secure if you are the only user or you can eliminate the security warning (e.g. by distributing the certificate).
I'm skeptical that any US based company could get away with not rolling in the face of a subpoena/NSL so the protection provided by the service provider knowing they have been compromised is minimal IMO.