I would, in every case, recommend using a passphrase that is at least as long as the encryption key length. I would expect that the encrypted email systems would be locking your private key (which MUST be at least 1024 bits, 2048 is better and 512 is worthless) under 128-bit RC5 symmetric encryption. That means, make your phrase over 16 characters long.
Also, never use any service which gives you your message in a webpage. If it doesn't maintain your messages in memory only, don't use it. Webpages are recoverable from your hard disk even after they are deleted. The only way to securely prevent recovery from a hard disk once data is written is to physically destroy the disk. If you happened to be under deep cover for the CIA and the KGB was about to sieze your computer and discover your illegal espionage activities, the only way to prevent them getting it off your hard drive would be to destroy the drive.
Keyboard monitoring is a problem, but so long as you don't let it in through a trojan horse, you shouldn't get hit with one. The authorities would need to break into your house and machine and install it. As an aside, it's possible to read the display contents of a monitor from a distance. The spooks put together a system where they analyze the RF emanations from your monitor and from that can "reverse engineer" what is on the screen. Your monitor is refreshing itself at a particular rate, and sending off radio waves as the magnets inside of it aim the electron guns across all the pixels on the screen. The signal it emits is different depending upon the combinations of pixels that are on your screen. So, by pieceing these together, they can reconstruct what you are looking at from down the street.