I put down the first draft a little bit, and checks for balance with a second look. Several critique / comments of my first draft:
1. For the early Upanisads, instead of picking a commentary, I am now of the opinion that the book selected should just be the texts of primary Upanisads, because a) Brahma Sutra is effectively a summary / commentary on Upanisads, b) the earlier / key Upanisads have been treated for a long time as one group; and c) Madhva commentaries presumably not too easy to be used to interpret Upanisads.
2. I am reading Songs of the Saints in India, and found myself liking the poems of Ravidas more than those of Kabir and Nanak. This gives me a stronger confidence that the selection should be Adi Granth (which includes works of all three) rather than just a selection of Kabir.
3. Indian philosophy-wise, based on Karl Potter's bibliography and his plan for The Encyclopedia of Indian Philosophies, I believe my selection is a fair representation (e.g. includes Umasvati to represent Jaina tradition, Udayana to represent Nyaya-Vaiseika, Abhinavagupta to represent Saiva philosophies, Ramanuja to represent bhakti Vaisnavite philosophies, etc.). The only "low representation" is for Advaita, and none included for the Grammarians and Purva Mimamsa. This could easily call for including Mandana Misra to be added to the list (he crosses this three tradition, and is the only non-Sankarite in the tradition, yet have influence to the Bhamati school namesaked after Vacaspati's work. I am still disinclined to include him though as after all is said and done, I feel among the 36 works with Upanisads, Sankara's Brahmasutrabhasya, Abhinavagupta and Ramanuja maybe the general lay of land for the Vedantic Indian philsophies are already well-represented enough. Also, the concentration of fame on Sankara may justify not diluting him with Mandana or a Kumarila who are clearly subordinated in later cultural memories.
4. I considered whether Ahmad Sirhindi and Shah Waliullah should be consolidated since they are in the same Sufi order. I still decided against this now as Sha Waliullah is more a scholar-type personality like al-Ghazali, while Sirhindi is squarely a mystic, though possibly a more intellectual one similar to Ibn Arabi. For representing the Chisti order (the most prominent Sufi branch in India, especially in the earlier phase), Amir Khusrow's inclusion in the list is key.
5. In terms of literature, I find myself possibly shorting the eastern lands (Bengal). Well, most Sanskritic literature are from North India, clearly well-represented. South is also well-represented with 2 Tamil (Ettuttigai, and one bhakti hymn set), 1 Marathi (Tukaram), 1 Maharashtran (Hala's Gaha Sattasai). West has at least one representative (Hemacandra is from Gujarat), but the East I have included no one specific in the original list. Looking at Bengali (also a language not represented), the clearly most important figure Tagore is too late in my overall scheme of things (I try to include texts up to 1899 at the latest), so instead, I would be adding Jayadeva's Gita Govinda to the second draft.
6. What to take out? My choice right now would be Tarikh-i Firishta - it is an important history work, considered canonical / authoritative during British India, but by now my sense is that it might no longer be quite as canonical. On the other hand, Abul Fazl at least still by the middle of 20th century was considered as a cultural luminary by Marshall Hodgson. And Abul Fazl also has the advantage of being considered a model for later Persian prose style.
So at this point the second draft would likely replace Firishta wtih Jayadeva. That is it for now!