Reddit mentions of The Nineteen Letters: The World of Rabbi S. R. Hirsch

The following is a list of basic books that will help you get a good handle on traditional Judaism. All the books listed are broadly recognized as being reliable, and many are considered classics in their own right:

• A Maimonides Reader by Isadore Twersky. An excellent compilation of the writings of Maimonides covering almost all of the most basic concepts in Judaism.
  
  
• With Perfect Faith by Rabbi J. David Bleich. This is an excellent introduction to medieval Jewish philosophy, based on Maimonides' thirteen foundations. Includes extensive lengthy quotations from many major Jewish philosophers.
  
  
• Path of the Just by Rabbi Moshe Chaim Luzzatto. Classic description of the ideal spiritual Jewish life. The opening chapter is particularly important for understanding almost all of modern traditional Jewish thought.
  
  
• The Nineteen Letters by Rabbi Samson Raphael Hirsch. An classic overview of Jewish thought presented in the form of a correspondence between a young rabbi and a childhood companion who is questioning the purpose and validity of traditional Judaism.
  
  
• The Stone Chumash - A good one-volume translation of the Torah, with an extensive commentary based on traditional sources.
  
  
• Ethics from Sinai by Irving Bunim. An excellent, three-volume commentary on Pirkei Avos, the Talmudic tractate that deals with ethics.
  
  
• The World of Prayer by Rabbi Elie Munk. An excellent two-volume commentary on the Jewish prayers.

I strongly advise that you don't do Daf Yomi. You should at least develop proficiency in gemora first, and before that you should at least become proficient in mishna. You can't really work through a gemora (and remember what you've learned) if you're covering a daf a day. It's definitely not a starting point. (Also, I would advise buying one volume at a time, as needed, rather than the whole set. But if you can afford the whole set, more power to you. It's a good thing to own).

I highly recommend a thorough study of Pirkei Avot as a starting point.

I haven't learned it myself, but Ein Yaakov is a renowned compilation of aggadata with commentary. I love the Maharal's derech in learning Aggadata, but it's not a place to start.

For an easy and thorough grounding in some fundamental concepts, I don't think the Nineteen Letters can be beaten (I several editions on Amazon, but I'm not sure who translated them. The only translations I know of are one from 1899 and this one. This has notes which are not necessary to understand it, but are valuable both to understanding the text and in themselves).

Advice for books is really, first and foremost, to learn something that draws you and speaks to you, and secondly something that you will be able to maintain. If you have ideas about this and want specific suggestions, I would love to help, but I don't believe that there are any essentials that everyone must learn. It has to be suitable for your personal style.

Besides for a chavrusa, I would also highly recommend a shiur and a fixed schedule (it doesn't have to be a big schedule — even 15 minutes once a week or five minutes a day — but obviously the more you can manage, the better (within reason, of course)).

I don't know how to learn Hebrew. What Hebrew I do know, I learned mostly from learning texts with a dictionary and/or chavrusa

Some general advice: I'm certainly not discouraging you, but it's important to pace yourself. For sustainable and lasting spiritual growth, you should focus on one small step at a time, and not focusing too much on the end goal (eg "to become a baal teshuva"). If you want to learn, or if some other mitzvah appeals to you, by all means take that on, and then when it's comfortable, take another... but don't worry about where it will lead you. Similarly in learning, rather commit to a little less than you're sure you can handle and build incrementally on that than risk biting off more than you can chew. I don't mean to discourage you at all, and I wish you the greatest success in your learning :)

Modern orthodoxy is mostly based on Tum

Torah U'madda- founded by R' Nochum Lamm read his book describing it.


You might also like Torah Im Derech Eretz- founded Rav Shampson Rafael Hirsch, I recommend his Nineteen letters.