Cross-country flying was one of the weakest areas for all my students. For whatever reason, they always had trouble with it. I'm talking about Instrument and especially Commercial students. I only had one guy who was almost always on top of the flight. Sadly, most of my students had gotten their ratings at our school, so that has something to do with it.

Come to think of it, I rescind my previous comment. Students have trouble with cross countries because they don't practice them enough. And that is sad, since that is what most of your personal flying (whether professional or just for fun) is going to be.

As an instructor, I'd advise you not to go to the same places all the time. Will you visit several airports more than once? Absolutely. Will you do the exact same plans every time? I hope not. Challenging your students will sometimes will challenge you, and it should. I hated going to the same lame places, so I always looked for new places to go. If I went back to instructing, I'd still have favorites, but always keep my eye out for a nice diversion or challenging airport too.