1) The Torah usually devotes itself to speaking about what G-d did, promised to do, or wants us to do. Our parsha is somewhat unique in that it spells out what G-d decided NOT to do, a hava amina of the RBSh”O, if you will. “V”lo nacham Elokim derech Eretz Plishtim ki karov hu…” Ideally G-d would have wanted to take us into Eretz Yisrael through the land of the Plishtim; however, lest the people clamor to turn back when faced with battle, Hashem instead took us around the long way.
The Chazon Ish is bothered by this “hava amina.” We know already from Parshas Shmos that Bnei Yisrael were destined to receive the Torah on Mt. Sinai, the mountain where Moshe saw the burning bush: “ta’avdun es ha’Elokim al ha’har hazeh.” Had BN”Y travelled north through the land of the Plsihtim directly into Eretz Yisrael, how would they have gotten to Sinai? Would they have entered Eretz Yisrael and then left again to get the Torah? It’s a simple pshat/geography question, but the Chazon Ish ends up with a tzarich iyun.
My wife suggested that we find that when Ya’akov was travelling to Lavan’s house, he passed by the makom mikdash but didn’t stop. When he turned around to go back, Hashem arranged for him to have kefitzas haderech so that he wouldn’t have to travel all that way. Rashi/Ramban disagree on how that happened: according to one view, Ya’akov’s route to the makom mikdash was shortened; according to the other view, the makom mikdash itself moved locations to come to Ya’akov. Why have Montezuma come to the mountain when the mountain can come to Montezuma? Here too, perhaps had BN”Y been able to enter Eretz Yisrael, Har Sinai would have come to them for the sake of kabbalas haTorah.
2) A number of meforshim are bothered by the fact that the pasuk first calls the people “ha’am” and then “Bnei Yisrael;” first we are told that the people will be scared by war, then we are told that Bnei Yisrael went out armed, as if they were primed and ready to fight. Ohr haChaim and the Maor v’Shemesh attack the questions from philosophically opposite vantage points. They share in common the assumption that the “am” and “Bnei Yisrael” refer to two separate groups, the “am” being the eiruv rav, the hoi poloi who tagged along, invited by Moshe to exit Mitzrayim with Bnei Yisrael, and “Bnei Yisrael” referring to the believers who G-d intended redemption for. The former group were liable to lose faith if the going got rough; the latter group were 100% committed to do whatever was asked of them. Their reading of how G-d's reacted to these two groups is radically different. Maor v’Shemesh suggests that the pasuk is telling us that G-d deliberately did not take the people through the land of the Plishtim because had they taken the short road, the “am” would have inevitably remained along for the ride. G-d's goal was to stretch out the journey in the hope (pen = maybe it will happen) that maybe they will fall by the wayside. The path through the midbar was a winnowing and weeding out process meant to discourage those who lacked fortitude from continuing. The Ohr haChaim goes in the opposite direction. G-d did not take the “am” through the Plishtim land precisely because it would have been too challenging, too discouraging, too difficult for them. “Ki karov hu” – the people, the “am,” have only newly (karov – near in time; products of the kiruv movement of Moshe) taken on the commitment to Torah, and therefore, too much cannot be demanded of them. (Parenthetically, this avoids having to read the word “ki” as “af al pi” [see Ibn Ezra, Ramban, Netziv]). The goal was to encourage the “am” to hang on, to accommodate their weakness, not to get rid of them.
Is it better to have a small, exclusive nucleus of strongly committed adherents, or better to be inclusive, to appeal to a broader base, even if the commitment of many will be weaker and diluted? That seems to be the issue Maor v’Shemesh and Ohr haChaim are grappling with. It’s the same issue our communities still grapple with: do you want to open a yeshiva for an elite group of top kids, or do you want to open a yeshiva that will educate everyone in the community, even if that means the classes need to go slower and the learning may be less intense? You can, I’m sure, think of other examples.