Comment Layers (Score 2) 109
You want security at the expense of usability? build layers!
A single system can be hacked, a single OS has bugs, a single app has backdoors, a single protocol has explots etc etc
Use LESS popular services in combination with layers of security. For instance; You can use the Tor Network to SSH into a proxy to tunnel chat with pidgin & OTR plugin. If you're even more paranoid assume your OS is already hacked, use some exotic image like Qubes, create temporary destructible VMs to carry information...there are options and many of them make basic functionality a nightmare.
If you really care that much about having your idle chitchat being "secure" you can always assume everything is being listened to. Good old fashion message encryption is probably much better than a special app.
I am quite happy there's more focus on security but let's be serious here, Tor is a target for snoops. they will find a way in because they already proved they can.