Joseph, we cannot enter Lebanon so the question is academic. Why be afraid of entering Jordan? The Jordanian authorities very much want tourism so there is a large police and military presence. This means very few terror attacks and little crime (although women travelling alone might have problems). of course, if one is a resident of EY one should know where EY ends so as not to be over on leaving for no good reason. In any case, I do not think that there is a mitzva to cover every millimeter of EY. In fact, there were anshei maaseh who never left Yerushalayim and today there are roshei yeshivot who almost never leave their yishuvim.
Quacky, how much depends on the individual’s level. Rav Kook once told someone that the first war Am Yisrael fought was against the king of Cheshbon to show that one must get rid of his cheshbonot. On the other hand, Rav Soloveichik asked a talmid how he would earn a living. Today some people do pilot trips and most speak to counselors at Nefesh b’Nefesh.
M.A., not to mention the fact that Ramban famously says that mitzvot are only obligatory in Shmutz laAretz so that they will not be forgotten.