I’m glad that my comment generated some responses. Here are some comments:
1) It helps if you are a voracious reader. I have been since my childhood days. That being said, it pays to read the best of the Charedi and MO world’s publications. I like Jewish Action, Mishpacha and the Jewish Press. The Jewish Observer is better than it was but the JO/ & Yated are way too ideologically driven for my taste.
2) There is no reason why anyone has to learn any sefer that is not either from a ksav yad or punctuated or both.
3) Find a good shiur, chavrusa and learn something. Daf Yomi without a shiur is manageable if you follow the Magid Shiur and look up some of the mareh mkomos. OTOH, a weekly shiur in Gemara is also important if you find a daily chavrusa too challenging. A rebbe helps unlock the ins and outs and what is happening in the Gemara , Rishonim and Acharonim.
4) Learning Chumash IMO means having a working knowledge of the Rishonim such as Rashi, Ramban , Ibn Ezra, Seforno and Rashbam and their respective ways of looking at a passuk. I will always have hakaras hatov to the JSS derech of learning “it and not about it” which gave me textual skills.Navi, as opposed to Chumash, becomes more and more oblique as Jewish history leaves EY until the time of Ezra. It also lacks for a Ramban style commentary with a global focus.
5) There are excellent sefarim which one could call likutim in Lashon HaKodesh on almost every aspect of halacha . This style of writing was pioneered by R Neubert’s Shmiras Shabbos Khilchasa. MB is wonderful if you have a punctuated text with the CI or Shoneh Halachos to compare it. I would not learn ShuT unless the teshuvah relates to a specific inyan that you are covering.
6) Hashkafa is some eyes a “third rail issues.” Zionism, the Shoah, college education, Daas Torah are all issues that either can be discussed in the prism of Jewish history in a non-judgmental manner or are completely off limits. That is a fact of life especially with the number of book bannings that have cropped up in recent years. IOW, if you are Charedi , you probably haven’t read anything by RYBS and if you are MO, you may not have seen the writings of many Baalei Mussar and Chasidus. You might not know that the inclusion of Mussar caused as much of a revolution within the Lithuanian yeshiva world as the development of Chassidus or that many RY survived haskalah and worse within their own families. I find the fact that Gdolim, not just BTs, emerged from such a setting much more of an inspiration than any hagiography that the subject knew all of Shas as a child and was a tzaddik. In fact, R Hutner ZTL wrote that we should not assume that the Chafetz Chaim achieved his madregah on lashon hara without a struggle. From my POV, I want to gain as much as possible from every Baal Machshavah within the Mesorah. One can always tell the breadth of a person by just glancing at a bookcase and seeing whether there is a broad range of classical seforim on every topic or just a lot of “klei sheni:” in English and ArtScroll., et al.