Can't even use Contact Us to do this. The dropdown only provides the accounts that are "active", I can't select the developer account that has not been renewed... and I don't want to select one of the other teams for fear of them shutting that one down instead. Can't initiate a transfer of ownership either, none of those options are available unless I fork up another $99 to renew the account.

Rebooting both devices does the trick for me, but would be nice for a fix so that all this rebooting doesn't have to constantly occur every time I want to work on one of my apps. Rebooting to fix issues is time consuming and annoying, rebooting to fix issues is such a "PC/Windows" thing to have to do. Part of the reason I love my Mac so much over my Windows PC was because I got away from stuff like this.