I'm going to have to jump through even more hoops to create a secure wireless channel.
What are you on about, you would sync it over an ssh/ssl direct connection and make sure the (cert) hash matches so you know you connected to the right device. Just get them on the same subnet and click sync on both devices (with a password you remember the first time). If you trust a third party it's a non issue to begin with.
I'm going to have to carry a cable around with me and deal with certificate exports and remembering to shred the files
If there is any every push to remove the need for remembering passwords there will have software to handle these problems. I am trying not to say how to do it because someone will create a system that the general public can make scene of and it will probably be better anyway.
Once you get over the need to have a password you can do far more tricky things.
Ideally each device would have its own key so it got compromised you could just revoke the key.