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A little complicated, but generally no. The ambient temp inside a case will be hotter than outside, how much hotter will depend on the specific case/fan configuration. Best to do solid recordings of idle/load temps of everything that has a sensor reading, then once you build it into your case, do a second set of measurements. This will give you a general idea of your cases thermal management, and areas which may need to be improved upon.
This. A lot of modern cases are designed around airflow, and because the fans are all directed at specific components, they can result in lower overall temperatures than you'd get in a bench setup where the air is free to flow anywhere (and therefore might not go where you need it to). It depends entirely on the case though.I submit it all depends on the setup, both bench and case. I think that most of the time bench will be running cooler but there are exceptions. For instance if your case is the one I am thinking of with the big fan up top and the 120's in the front that can be moved around, I can envision a case fan configuration that would provide better cooling in the case for both the CPU and the mosfets around the CPU area.