It might be best, in U. S. philosophical education, to begin by studying intellectual strategies natural to people in the United States. Reading The Metaphysical Club, Louis Menand's tour through U.S. intellectual history since Emerson, one finds lots of familiar moves: what one has been inclined to say, what was said around the house, what one heard from the pulpit. It might be best to see that mass of intuitions whole, at the start of one's philosophic career -- to understand how U.S. thinking responds to U.S. circumstances, geography, modes of life -- how certain conceptions come to seem natural to us.
We can understand particularly well how a particular conception could come to seem natural about those conceptions that have come to seem natural to us. We can see how beliefs are woven into our lives, supporting them and being supported by them.
Other people's conceptions take more work. When one reads Simone Weil's The Need for Roots, one has to keep in mind that her project is, in large part, to keep France from becoming like the United States, to keep France from losing continuous traditions and history of which U.S. citizens can have no first hand understanding. One has to a approach a work like that with a sense of U.S. peculiarity.
Of course, greater feats of imagination are needed to get close to Aristotle or Descartes.
Wouldn't it make sense to explore first what it is to be at home in an intellectual tradition, and then to try to understand foreign traditions?