On the PickKit2 video, I felt Dave was pretty open and honest about his experience - and one that I'm sure many, if not all, of us have encountered at least once.
Yes, he had frustrations. Yes, he had a dummy spit or two - but anyone watching who didn't have any advanced knowledge of the PickKit2 (such as myself) could understand the battle. You might also recall that when Dave found out the 'secret' that he was quite open in sharing that.
Software version compatibility issues, such as he experienced, are a last century subject. We really shouldn't expect this sort of thing in a modern day bit of kit. So when these things do raise their ugly head, you get the same reaction as Dave ... He just had the pluck to publish it - whereas I would just sit quietly and reflect upon my experience in the safety of my solitude.