As sad as it is to say, lets be honest and admit that this is a fairly small number. How long do you think it will be till your less committed friends get tired of decrypting your emails and just ignore what you send? Make sure you only pick people that use actual email clients because gpg and Gmail is no fun.
As far as the "Thomas Crowne Affair attack" goes generating effective cover traffic is not easy and random traffic is definitely a bad idea. Basic traffic analysis would be able to separate your legit emails from your cover traffic.
Addendum: I noticed you just generated your new gpg key yesterday. Why not go big and use a 4096 bit key?
https://chrome.google.com/webstore/detail/mailvelope/kajibbe...
(I suspect that'd last about 121 minutes before most of my friends spam filtered me forever)
That, sir, is genuis. Now that talibans have office in qatar, I hope they'll publish some kind of contact email, so we can rickroll both NSA and them through tormail. Sorry authoritarians, this is the internet.
Repurpose Sircam to do this, perhaps.