We checked into Eielson AFB for a training detachment once and during the in-brief ATC informed us not to make 'courtesy calls' to them and to check in with all of the information they required of us on initial contact.
I told my students that we would try it and play by their rules, but that it was my experience that it would lead to missed calls and therefore more unnecessary radio traffic. After day two of making the initial calls without any heads up, and having to reiterate the string of information after numerous "Raider XX say again", we went back to doing things the *old* way.
You get a feeling for when such calls are required and when they aren't. I'll use my own judgement and not worry about being "that person". Real life isn't quite so neat. Of course I still fly with a few who still use "with you" too