I am a big believer in appreciating seforim on their own terms. There are multiple ways to skin a cat and answer a kashe, and a pilpul of the Chasam Sofer is no less interesting or valid than a distinction of R’ Chaim Brisker. The key to unlocking and enjoying a sefer is to accept the terms of the system being used, the boundaries of the thinker’s paradigm, and then exploring how the author maneuvers within it. Stepping outside the box and comparing and contrasting paradigms is interesting, but some people get so bogged down in defending one system over the other that they never come to any appreciation for the genius of the maneuvering and navigation and chiddushim that can come out of a system different than the one they are locked into.
I remember once posting about the twists and turns the Parashas Derachim takes us through in exploring how the Avos kept the entire Torah, with every detail, and at the same time retained their status as bnei Noach. A ben Noach cannot keep Shabbos – what did the Avos do? How did Ya’akov marry two sisters if he kept the Torah? Some people were not even willing to entertain the question because they never got past insisting that the Avos had some general sense of commitment but not did not observe the details of every mitzvah d’oraysa and derabbanan. The torah and genius of the Parashas Derachim are a closed book if you reject the frame of reference needed to set up the question. Or to take another example, if you cannot accept using a mystical framework to read chumash, you have basically shut the door on hundreds of seforim whose insight might enrich your avodas Hashem.
I have noticed that the Ayeles haShachar of Rav Shteinman on chumash adopts the same paradigm or framework as the Meshech Chochma, the Netziv, Maharal Diskin, and especially the Brisker Rav and the Rogatchover, and others. These gedolim read every detail in chumash (and Rashi) as having halachic import or explainable on purely halachic terms (and I know that is a gross oversimplification and exaggeration, but in one sentence I can’t do better). For example, in the post I did earlier on why Ya’akov felt bad about sleeping where he did, the Brisker Rav comes up an explanation based on the halachos of morah mikdash rather than practical, moral, or theological reasons.
Every now and then I find a question where it seems that the boundaries of the paradigm create the real stumbling block rather than a path for a solution (similar to the way the Parashas Derachim's understanding of the Avos' shemiras hamitzvos creates a set of problems that he then resolves, but which might not exist if not for the framework he adopts) and I wonder if there is a deliberate attempt to find an answer that works within the thinker's framework or whether the whole thing operates on some unconscious level and once you are submerged in an approach it eclipses other solutions. You could ask this question in any number of contexts; I raise it here for no other reason than it hit me again when I saw this question of Rav Shteinman on VaYeitzei:
Ya’akov meets Rachel and the Torah tells us, “VaYisa es kolo vayeivk,” Ya’akov cried (29:11). Why was he crying at this moment? Why does the Torah mention his emotional reaction to meeting Rachel? Rashi explains that Ya’akov cried because he saw prophetically that Rachel would not be buried with him.
Rav Shteinman asks: So what? Why should that have upset Ya’akov? He answers that there must be a “sibah meyuchedes” for the Avos and Imahos to be buried together (see Baba Basra 58), but he offers no further explanation of what that "sibah" might be. He also cites (but does not think it is compelling) a ShLa”H who explains that Ya’akov saw that Rachel would be buried on the road as a comfort to the Jewish people headed to exile. Ya’akov cried over the destruction of the Mikdash and that future exile.
Now, call me romantic, but I don’t see the question. Ya’akov has just met the woman whom he will marry. The Torah tells us that “Vaye’ehav Ya’akov es Rachel” – Ya’akov loved Rachel. We know that Ya’akov’s relationship with Rachel was special; she was the akeres habayis. Given all that, is it really hard to understand why Ya’akov would be upset over the fact that the woman who he loves will be buried along the road and not share a grave with him?
Rashi offers another explanation and attributes Ya'akov's crying to the fact that he has come empty handed. Here it is Sifsei Chachamim who asks: So what? Why cry over a lack of money? A tzadik places no value on material wealth. Rav Shteinman answers that Ya'akov did not cry for the loss of money so much as what money represented: the loss of opportunity to do chessed. But why not cry over that loss earlier, when it occurred? Again, the romantic answer is obvious: it's not just the loss of the opportunity for any chessed which troubled Ya'akov, but specifically the loss of ability to greet his future wife with the proper gifts that would be expected of him, the specific chessed (if you want to call it that) which must be shown to one's spouse.
Does reading Rashi with Rav Shteinman's lens in this case solve a problem that the average reader would get stuck on or create a problem that the average reader would not be troubled by? I guess the answer is "It depends" -- is the average reader a romantic or a dispassionate observer? Do we understand emotionally the grief of not being buried with one's beloved, even if it has no halachic justification? Does it sit easy with us ascribing that sense of emotional grief to Ya'akov, or at least reading Rashi as doing so?
One need not pick and choose between these approaches or the many others that are possible. Every approach unlocks questions that we otherwise might not have asked and offers answers that we otherwise might not have thought of, which is what makes learning so interesting and rewarding.