I love the idea of two factor auth, and I think Google has generally done a good job on it, they have certainly tried to make it easy to use .
But the collision of iOS/OSX and Google TFA is just killing me. The problem probably lies in the Apple products — when you configure a machine to do imap email PLUS smtp send PLUS calendar sync PLUS address book sync, it is just broken. The application specific password provided by google has to get squirreled away by all these apps and it doesn’t appear to work, I consistently have problems keeping SMTP send working. I’ve tried recreating the application specific password multiple times and I always end up broken somehow.
Google is not without fault tho. I have two google-hosted accounts I use regularly — a gmail.com account and my theludwigs.com account. When I try to configure the security settings, the Google web pages get super confused about which account I am in. I’ll try to set the security settings for the theludwigs.com account and I get the page for the gmail account.
So for now I am giving up.