Yeah, upgrade guides would be quite nice, although in my experience Checkmk was always painless and dead simple to upgrade, so my main concern is compatibility within the upgrade process and rather shortly after.
I am waiting for quite some time now for some features in 2.0 so I want to upgrade really soon after the release. That’s why waiting for the conference is not my preferred scenario.
But maybe someone with deeper insight can add a little confidence here. 
But thanks for your input @aeckstein!