In my experience installing updates to Jenkins has been painless, 2.0 was no different.
That being said, I updated a few instances to 2.0, immediately applied all plugin updates and things kept working as before. That was a surprise. I was already prepared to spend hours trying to find why our jobs were failing. That was nice.
I was already prepared to spend hours trying to find why our jobs were failing.
Yeah, that's exactly what I'm not prepared for, and trying to avoid. :-) No one pays the little Mac Mini on my desk much mind...until it doesn't work.
In my opinion, Jenkins is a product that you really need to have a test instance for, where you either have copies of your builds or you've set up some 'unit test'-type builds to exercise functionality you depend on.