I'm looking to spend about 3 months learning Jewish philosophy pretty intensely. I'm looking for recommendations on what are the best books to read, which ones may be too complex, and how I should balance the study of the Torah, Prophets, and Writings with more contemporary texts.
Thank you!!!
You might be interested in Books of the People: Revisiting Classic Works of Jewish Thought which gives you a sample of core books of Jewish philosophy, specifically "ten foundational books written between the tenth and the twentieth centuries that have dramatically influenced the development of Jewish thought".
The list of the ten books is in itself one answer to your question
If you had to start with one classical book, it would be (in my personal view) Rabbi Judah Halevi's Kuzari, e.g., in this very good edition. And if you decide to "attack" the Guide of the Perplexed of the Rambam, you might find this summary book helpful at first.
Jewish philosophy is an oxymoron.
Judaism is Torah which is the Divine and Rabbinic Instruction. Mental sophistry is extremely dangerous and even logic can lead to wrong paths relative to the Torah.
EDIT:
Citations
Sichot Haran #40
Regarding the books of the m'chaqkrim (philosophers) it's already explained by us many times that it's forbidden to delve in them, and one needs to stay utterly far from them without looking at them at all. Even the philosophical works of gedolei Yisrael. For it's a severe prohibition to study them (and it's already explained in many holy books the great prohibition of studying them). For such things are not the portion of Jacob (Jer. 10:16, 51:19), and we have nothing at all to do with them. For we are true to His Blessedness in Emunah alone, without any probing, that His Blessedness created the whole entire world and sustains His world and will in future time renew His world, and for this we don't need philosophy. But the way of these books is to ask questions that appear very difficult, while providing very weak answers. And whoever wants to probe deeper and question that answer, he can refute the answer and render it completely useless. Therefore we may not study these works at all. So in truth all their questions themselves are nothing, and they are mere vanity and striving after wind (Eccl. 1:14).
The fact that we see there are people who are not drawn to the utterly holy and awesome books such as the Zohar and the Ari's books of blessed memory and so forth, even though they have utterly, utterly wondrous novelties that enlighten the eyes and are sweeter than honey (Ps. 19:9,11), but they are drawn specifically after other matters such as philosophy - Know that this is due to their inborn nature, for their their natural character is a bad from birth, that their were born with an evil temperament, that they cannot tolerate a truly holy thing. (B. Rabbah 28; v. Sichot Haran #32). But having been born with this bad temperament, he needs to endure great bitterness to break this evil temperament and nature. Fortunate is the person born in holiness!
In the [philosophophical] books are questions regarding the order of creation. They may ask why was a star worthy of being a star, or a constellation a constellation, while other things were consigned to lower realms, such as beasts, animals and so forth, why were they not [humans] the other way around? Or they may ask why the head is what it is and not a foot. Questions like these are discussed at length in such books. But it is all vanity and striving after wind. And there's no need to question His Blessedness, for (Lam. 1:18), "Righteous and upright is He."
In truth, know this! The whole world is a rotating wheel (B"B 16b) - like a dreidel. Everything turns around and reverses. Man becomes angel, and angel becomes man. Head becomes foot, and foot becomes head. Similarly everything else in the world reverses, alternates, and swaps, from high to low and from low to high.
For in truth at the root it's all one. For there are transcendental beings namely angels, that are entirely detached from the material, and there are celestial spheres that are the in the aspect of materiality but their "material" is extremely refined, and there is the lowest world, which is completely material. But even though all these three are from different realms, nevertheless at the root, there it's but one. Therefore the whole world is the aspect of a rotating wheel and everything turns and reverses. One moment something is in the upper aspect, the aspect of the head, and another thing is in the lower aspect, the aspect of foot. Then the situation is reversed: head becomes foot, and foot becomes head. A man changes to an angel, and an angel becomes a man. Like we find, that our Sages obm teach us that angels were cast down from Heaven to the base world, entered into physical bodies, and were subject to all worldly lusts etc. Other angels were sent on missions to our world and clothed themselves in physical bodies. Conversely we also find cases where human beings literally became angels. For the world is like a rotating wheel, like a dreidel, everything in motion. For in truth at the root it's all one, as mentioned. (We also find the foot of one is also higher than the head of another. Likewise in the spiritual worlds, the lowest level of an upper world is higher than the highest level of a lower one. But in truth everything rotates as mentioned.)
And this is the aspect of playing dreidel on Chanukkah, for Chanukkah is an aspect of the Holy Temple (see L"M II:7). The main concept of the Temple is the abovementioned, the revolving wheel. The Temple represented "the superior below and the inferior above” (Pesachim 50a; Bava Batra 10b). For H"Y lowered His Presence into the Mishkan and the Holy Temple - this is the aspect of "the superior below." Conversely the form of the Temple, it's all engraved on high and this is the aspect of "the inferior above." Which, this is the aspect of dreidel, a rotating wheel, that everything revolves and swaps levels as mentioned. For by Charika/philosophy/logic it's an inconceivable thing, that H"Y, who is above and beyond all etheriality, should constrict His Shekhina into the vessels of the Temple. "Behold, the Heaven and the Heaven of Heaven cannot contain You; how much less this Temple?" (I Kings 8:27). Nevertheless H"Y showed that he is precisely the opposite of their opinion, for in truth H"Y the root of his Shekhina is in the Mishkan. Similarly it's inconceivable according to Chakira that mortal man who is a lowly being should have an impression on high. Or how a lowly beast they sacrifice it for an offering that it should ascend "as a sweet savor" giving pleasure before His Blessedness, as He spoke and His will be done (v. Rashi Zevachim 46b). And how can desire apply to His Blessedness?! But in truth H"Y showed, opposite to their mind, for in truth H"Y placed his Shekhina below in the Mishkan and the Holy Temple, and the beast rises as a "sweet savor" etc. So this is the aspect of the superior below and the inferior above, the aspect of the revolving wheel, the aspect of dreidel.
And behold, the power/potential of Heyuli (Ether) brought in their [philosophical] books, is the aspect of the intermediate between Koach/potential and Poal/actual. For everything initially is potential and then actualitizes. And when it goes from potential before it comes to actual there is the aspect of Heyuli which is the intedaiate between potential and actual, which is the root of all creation. For they all go out from the potential of Heyuli, for they were all intitially in the aspect of the Heyuli's potential, and creations going out from there which are the three abovementioned aspects, which are: transcendental, celestial, and material - they all change places, transcendental to material and material to transcendental and so forth with all of them, for at the root it's all one as mentioned. And this is the aspect of the letters inscribed on the dreidel, which are Hei, Nun, Gimel, Shin, acrostic of Heyuli, Nivdal/transcendental, Galgal/celestial, Shafal/material, which encompass all creation as mentioned, which all turn in cycles, alternating and revolving, one thing becoming another as mentioned. Which, this is hinted in Chanukkah, which is the aspect of dedication of the Holy Temple, where "the superior is below and the inferior above," which is the aspect of dreidel, the aspect of the turning wheel where aspects interchange as mentioned.
And this is the aspect of the Redemption, for this is the essence of the Redemption, which will be in this aspect, namely the aforementioned aspect of turning, the aspect of superior below and inferior above that was in the Holy Temple. Therefore when they left Misrayim immediately at the Song at the Sea they said, "You brought them and planted them on the mount of Your inheritance... the Temple, H', which Your hands established" (Ex. 15:17). That they heralded the building of the Holy Temple, for the essence of the Redemption was that the Holy Temple be built, where would be the aforementioned aspect of the revolving wheel, the aspect of superior below and inferior above (which is the essential ultimate purpose), for in truth it's all one, for at the root everything is one, as mentioned. This is also the aspect of the aforementioned letters, which are H N G Sh - acrostic "Gaalta Shevet Nachalatekha Har Tzion - You redeemed the tribe of Your inheritance, Mount Zion" (Ps. 74:2) - the aspect of "You brought them and planted them on the mount of Your inheritance," the aspect of the Holy Temple, as in that place was the aspect of the turning wheel which this is the essence of the Redemption as mentioned.
And see the essay (LM II:7) on Chanukkah that begins, "And it came to pass at the end" (Gen. 41:1) and, "The merciful one will lead them" (Isa. 49:10). There he explains also the matter of the superior below and the inferior above, as well as the fact that Chanukah commemorates the rededication of the Temple, see there. And this is the aspect of the Maqifin/surrounding powers discussed in this lesson, namely the aspect of the turning wheel, namely the dreidel, is the aspect of surrounding and turning. Study the lesson carefully and understand. (Chokhmah is the aspect of Heyuli).
Returning to our original discussion: We have no need to enter at all into philosophy, which is anyway strongly forbidden. We just need to keep true to H"Y in Emunah alone, that His Blessedness created all the worlds entirely, sustains all of them, and will in the future renew His world.
See also Chayey Moharan #407-425 and many other Chazal, Rishonim and Achronim vehemently against the severe prohibition of studying philosophy even "Jewish philosophy."
