There are I think no objections to the way philosophy is taught to undergraduates today in US and UK universities. Courses are on the whole very well taught, there is a an emphasis on clarity and often on originality, and students learn a great deal of respect for decent argument, as well as sound scholarship. Courses on the history of philosophy have never been better, and this is true of courses in other areas as well. I believe you when you say that your school philosophy courses was too broad and "even the professors seemed overwhelmed with the readings." I have noticed this kind of thing before. You are absolutely right that "specialization results in a greater degree of understanding", though there is a place for the well-taught survey course. If I were going to offer a course on three philosophers, I would want the three to have a strong link, so for example a course on "Descartes, Spinoza and Leibniz", "Stewart, Reid and Hamilton", or "Russell, Moore and Wittgenstein".
How about Leslie Stevenson's Ten Theories of Human Nature? I have had good luck teaching freshmen with this, doing a course called "Human Nature". It's on Amazon at
Good luck with the class!
Answer to Q1: Why should a person who loves philosophy not steer towards academic philosophy? The better one knows her the more she has to offer, such as fascinating arguments. Answer to Question 2: If you are in love with someone, you really should marry that person, other things equal, no? Philosophy can be difficult sometimes, even temperamental, but she is not mad.