Stop using Skype. The NSA allegedly collects all Skype traffic anyways. Do you really want that? "The full capture of voice traffic began in February of 2011 for “Skype in” and “Skype out” calls—calls between a Skype user and a land line or cellphone through a gateway to the public switched telephone network (PSTN), captured through warranted taps into Microsoft’s gateways. But in July of 2011, the NSA added the capa…
I've given up on the NSA not reading my stuff. The NSA collects pretty much anything they can get their hands on. It's a losing battle. If there's something I don't want the NSA to know about, I use Tails.
This is a nice thought, but probably not realistic for a variety of reasons. Perhaps most relevantly, I would expect that a large quantity of major Tor exit nodes are tapped by the NSA.
I would also expect that most servers you talk to are either already tapped by NSA in one way or another or can be tapped by the NSA trivially if they decide they want to see what's happening.