I have had people, including my wife who is also an educator, tell me that I expect too much from my students. How do you tell when you are not only challenging them but asking too much of them?

I have a lot of students who show attributes of both age and disability issues where they are both adult learners and also they had problems when they were in school decades ago. How do all of you handle students who still have the problems they had 30 years ago but have even more complexes about them now?