I have the same issue. Just spend 30 minutes chatting with multiple people. While waiting for them, I opened an account at tax1099.com, and filed.
In the end, it appears the issue for me was that "track payments for 1099" had to be checked. This can NOT be found on the "contractors" page. This can NOT be accessed via the 1099 payment page. It has to be accessed by going to expenses > vendors and then selecting vendor and clicking "track payment for 1099"
I guess in the end I win though, because the cost for filing with tax1099.com was far lower than Quickbooks would have been. I'll continue to use them in the future too.
The poor design, as well as poor customer support at intuit is beyond my belief.
