Also, if your platform supports it, Gmail has perfect forward secrecy meaning that even if the NSA records all HTTPS traffic to gmail and later demands Google's private key they can't decrypt any of that captured traffic.
Tor on the other hand is a problem. It has several fundamental flaws as you pointed out like by controlling some gateway nodes and a few others you can start breaking any sort of secrecy that you would get from Tor. Really the only good thing about Tor is that it's well known. I really wish Tor would just die and people would move over to something better like I2P where it's an anonymous network, not just a kludged together anonymous proxy with hidden services slapped on as an afterthought.