It pops up a dialog saying do you want to update your help and if you view the Output then 447MB later of downloads (on the Mac), it starts updating. But next time you run Visual Studio the same thing happens?
It’s not you, it’s the version of the help is 6.0 even though you are on 6.1 (according to the Xamarin Bug Log). The quick fix is to download the help manually. As Xamarin engineer Jose Miguel Torres say in the bug report:
“Open XCOde and go to Xcode menu –> Preferences… Then click on Downloads tab and switch from components to Documentation.There should be the iOS 6.1 DocSet entry and the most probably is that it is not installed. Click on Check and Install button from the Xcode dialog and wait for the iOS 6.1 DocSet to be installed. ”
After that, you should see the Mac Server Log
[2013-09-01 10:22:44.2] Using https://developer.apple.com/rss/com.apple.adc.documentation.AppleiPhone6.1.atom
[2013-09-01 10:22:44.9] API Docs installed version: 18.104.22.168
[2013-09-01 10:22:44.9] API Docs official version: 22.214.171.124
[2013-09-01 10:22:44.9] Command [StatusSdk: CommmandUrl=StatusSdk] finished (9)
No more update requests.