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Regarding technical issues, the biggest time wasters are build issues for iOS. We use MSBuild for our build process and the iOS Visual Studio integration seems to break often unless you are continuously developing with iOS and keeping all the tools up to date. I attempted to update to Xamarin 4 but had to rollback due to compatibility/build issues that I did not have time to resolve. Considering my dependency on MSBuild I am often concerned that new updates will break any integration that I was previously able to implement.
RE: the specifics around the issue:
The issue is difficult to nail down, on one repo/branch it is able to build fine, while in another Visual Studio complains about a Build Host version mismatch even though the project files should be the same in both.
Xamarin.iOS (VS): 188.8.131.52
Xamarin.iOS (Mac): 184.108.40.206
Xamarin Build host: 220.127.116.113
XamarinVS 4 included a significant major change on how Xamarin connects from Windows to Mac, which was the Xamarin Mac Agent (XMA) using SSH instead of the old Build Host approach.(https://developer.xamarin.com/releases/vs/xamarin.vs_4/xamarin.vs_4.0/#Xamarin_Mac_Agent)
That was a needed breaking change, as it enabled tons of improvements on our product.
After that change, which requires a different setup on the Mac (Enabling Remote Login) and in your build script (as it requires Mac credentials), newer builds shouldn't break anything in that place.
In XVS 4.1 (current Beta) we are also supporting command line builds connecting to the Mac using parametrized SSH Key authentication, including passphrase. If that setup fits better your case please let me know.
One thing we cannot resolve (yet) is that Windows and Mac needs to be updated to the same compatible version simultaneously, However, starting with XVS 4, we're allowing to build it successfully even without updating Windows (unless the changes on the x.iOS Build system make it to fail).
I agree this is an issue moving from XVS 3 to XVS 4, and it used to be an annoying issue with the old Build Host (XVS 3 and older versions), but starting from XVS 4 I think this scenario has been improved significantly.